sparr

The internet peaked in 2008

The year is 2008. You don't know it yet, but the internet will never again be as accessible, searchable, interoperable, or durable as it is right now. Profit motive, the tragedy of the commons, and malicious self interest are beginning to conspire to erode all of the best parts of the online world, and it will only get worse from here. Here are some of the highlights of your regular online experience that the people being born today won't even realize were taken from them:

You open up your RSS reader and see a chronological list of updates from every website, blog, etc that you are subscribed to. You can sort and filter to the topic categories you've created. You can jump back to the last time you read, to make sure you didn't miss anything on the feeds that are important to you. When you visit a new site or page, if it has a regular flow of new content then it almost certainly publishes a RSS feed that you can subscribe to.

You buy a copy of a multiplayer online video game. It either includes a dedicated server application or has a server built into the client. You can play against your friends without accessing the publisher's servers or paying any recurring fees. You can play without an internet connection if you're on the same home network. You can still play online even when the developer and publisher go out of business in the future.

You open your favorite instant messaging client, one of half a dozen independent options (Adium, Pidgin, Trillian, Miranda, Kopete, etc), any of which can connect to almost every major messaging network (AIM, MSN, Yahoo, ICQ, Google Talk, Facebook Chat, etc). In that single window you see all of your contacts from every network, with the same contact on multiple networks merged for you to choose between. Your friend Sam is online/reachable on four networks; do you want to use the one that supports images or typing updates or voice chat or encryption? Your friend Pat is offline across the board, but left a status message saying where they were going.

You see something cool and want to share it with a friend. You copy the URL and message it to them. They can almost certainly view the thing without creating an account or logging in somewhere. You scroll back a year or a decade in your chat with them and the links back then probably still work.

You make a post on a social media/network platform with a link to some other platform, and the content from that other platform is automatically previewed or embedded in your post. Your friends can watch your Youtube video directly on your post in their Facebook feed. You don't need to screenshot a tweet to get its contents to appear on another site.

You search for something on Google. The first page has a single relevant text-only ad, and ten results that are virtually guaranteed to be the best available resources for your chosen topic.

You search for restaurants near your home that offer delivery, and that's exactly what you find, with their menus and prices listed directly on their website.

You launch a program that you installed five years ago, and it still has all the same functionality it had before. All the servers it interacts with still support the same protocols. All the file formats it can read and write are still compatible with other newer programs.

You take some time to chat with people who share your niche interest. There's a single IRC channel and one web forum where almost all of them congregate. The content of at least one, possibly both, are indexed by major search engines, and you don't have to create an account to read past discussions.

You launch Google Chrome, excited for another open source entry into the browser war and the diminishing dominance of Internet Explorer. You have no idea how short lived the impending era of vaguely balanced browser market share will be before the pendulum swings right back to a single browser controlling the market.

You're a somewhat technical computer user, but you have a niche question that only a few other people would know the answer to. Luckily for you, Stack Overflow launched recently, and is already rapidly becoming the single best resource the world has ever seen for this scenario. You post your question and get helpful answers from well qualified people in short order.

You use a minor internet and email provider, perhaps a local ISP or through your work, or even hosted on your own. Your emails reliably reach users on all other major and minor email providers, without automatically being classified as spam.

You use Google Reader, Yahoo Pipes, iGoogle, Meebo, Delicious, or other such web-only apps, with no idea that they will simply disappear some time soon.

Over the next ten to twenty years, these experiences will become fading memories. Mentioning them will make you sound more and more alien to younger people. Some of them will leave the Overton window entirely and even arguing for them on their merits will start to sound unreasonable. We won't just forget these experiences existed; we'll stop imagining that such things are even possible. Maybe if we're very lucky some of them will eventually be reinvented from first principles. Thankfully, it's still 2008, and you don't need to worry about any of that. Party on.

PS: Each individual aspect of online technology described here actually peaked at slightly different times, ranging from the late 1990s to the early 2010s. I chose 2008 in this article as roughly the peak within that range, to accommodate a few specific landmark dates, and as a symbolic nod to the people born then becoming adults now. While you could make some of the same arguments about 2002 or 2012, the overall pattern wouldn't be nearly as strong.

Doing chores is a normal part of living alone and it gets easier together.

Almost everyone does chores in their living environment or compensates someone else for doing them. This is a perfectly normal aspect of being a functional adult. Maybe if you live alone and have low standards you don't do many, but you still have to at least occasionally do some laundry, take out some trash, shovel some snow, etc. Maybe if you live with one other person you split the chores, or one of you does most of the them and the other pays most of the bills, and hopefully you both consider that a worthwhile trade. If both people in a couple have jobs and split the bills, most of the people I regularly interact with understand that it's unreasonable to expect one of them (probably the woman) to do all of the housework. These all seem to be well understood concepts in our society. No one is confused when these scenarios are assumed background for a conversation or piece of fiction or proposed policy. Everyone understands when divergence from these norms is assumed to be problematic.

Somehow, all of that goes out the window when discussing living with larger groups of people. Most people hear about an expectation that they do their share of the household chores in a coliving environment and respond with things like “I can't work a job AND do work at home” or “I'm not signing up for a second job” or “Are you going to pay me for all of that work?”. Somehow, those same 2-5 hours a week that they would have spent on laundry, dishes, trash, snow, lawn, sweeping, etc living alone becomes “not my job” as soon as they live with other people. Oddly, they see this as somehow fundamentally distinct from the same statement made by a man who moves in with a woman, which scenario they would strenuously object to. Further, this isn't just self interest; many people still feel this way when discussing other people in the same situation. There's something about the larger group that fundamentally changes people's understanding of household responsibilities.

The situation is even worse, from my perspective, because I advocate for the economies of scale in coliving. When a bunch of people pool their resources, including their labor, everything should, and usually does, get easier. Mowing a single big yard takes less time than mowing a bunch of smaller yards. Cooking dinner and washing dishes for 20 people is significantly easier than doing it ten times for two people. This pattern continues across almost all chores. So, when someone rejects the idea of coliving chores, not only are they breaking a norm that exists even in smaller groups or for individuals, they are also somehow making it sound like more hardship despite it being less work than it would be otherwise.

It gets worse again when you consider the benefits gained by consolidating the resources behind those chores. Hopefully, they've made a good decision about the environment they want to live in. They'll enjoy that big yard more than they would a tiny yard. They'll enjoy those group dinners more than they would eating alone. They'll enjoy a larger home theater, a bigger garage, and so on across all the other experiences and amenities they'll be able to take part in that they wouldn't otherwise. So, now they aren't just complaining about doing the same work they'd be doing living alone, or even about doing less work than living alone, but they're complaining about doing less work for more benefit!

How does someone get from “Spending 30min/wk doing dishes from eating alone is necessary” to “Spending 20min/wk doing dishes from dinners shared with my friends is unacceptable”? I have never been able to wrap my head around this in a charitable way. I am hopeful that someone reading this might be able to offer some insights that will better inform my future engagements on this topic. Since I don't plan to stop founding intentional communities, I expect this will continue to be an important recurring conversation in my life.

PS: For reference, the last large scale chore system I developed for a ~20 person household required each person to do three chores per week, with about 1/3 of the available slots being cooking communal meals and maintaining our most active kitchen, and the other 2/3 covering everything else. One version of those chore descriptions is still visible online here: https://docs.google.com/document/d/1797qiZ5iODelLS6oZm41gwEhtlMcttHfrG6CYM0c7Q4/preview

Accurate Confidence is a Trainable Measurable Skill

Without looking it up, who was born first, Mother Teresa or Ronald Reagan? Spoiler alert, they were born six months part, so very few people will know enough historical trivia to get this right other than by luck. It would be a coin flip for me. Everyone seems to be comfortable with the idea that you can seek out and learn more historical facts and other trivia, increasing your chances of getting questions like this correct. Now... How confident are you that your answer is correct? Very few people seem to be aware that you can learn to be better at this second question. Many people even deny that it is possible for one person to improve that skill or for someone to be better at it than someone else, let alone to measure it.

There are a few well known ways to demonstrate the existence of this skill and to measure it. A useful search term is “confidence calibration”, which will lead you to various tests and assessments. An acquaintance of mine previously compiled a list of such exercises at https://www.lesswrong.com/posts/LdFbx9oqtKAAwtKF3/list-of-probability-calibration-exercises.

One popular version (“confidence rating”) asks you a series of questions with fill in the blank or multiple choice answers, then for each question how confident you are of your answer. For a fill in the blank question the confidence range might be 0-100%, while for a multiple choice or binary question the floor is usually equal to choosing an answer at random (e.g. 25% for 4 answers). If you have well calibrated confidence, the results might tell you that when you were 70% confident your answers were right 68% of the time. If you have poorly calibrated confidence, that result might be 50% or 90%.

Another version (“confidence interval”) will set a particular target confidence (e.g. 80%) and ask you a series of questions with numerical answers (dates, weights, counts, etc). Instead of a single answer you give a range that you are 80% confident the answer falls in. At the end, if the true answer was in your range about 80% of the time, that's a good outcome, but if the true answer was in your range 50% or 95% of the time then there's a lot of room for improvement.

When someone without practice evaluating their level of confidence takes a confidence interval test targeting 90% success, they will usually succeed 30-60% of the time. When they take a confidence rating test, their confidence will correlate to their actual success rate similarly poorly. In my experience, a single demonstration of this outcome, alongside the results of someone with more calibrated confidence, will often suffice to convince them that there is something to this idea.

This skill extends beyond trivial examples and tests. It applies to far more impactful scenarios like planning professional projects, scheduling travel, buying stocks, signing a contract, negotiating a lawsuit settlement, etc. If you recognize this skill in yourself, it will allow you to make more effective decisions toward your goals. If you recognize this skill in others, it will better inform your reliance on their predictions and claims. Denying that this skill exists, or that you and other people can get or be better at it, will lead to less optimal outcomes in so many ways.

My goal in writing this post is to be able to link to it in the future when I encounter one of those people who don't believe this skill exists. Maybe at least a few of the people who aren't willing to take such a test themselves will instead be willing to have the nature of such tests explained to them, and a few of those will understand it enough to realize their mistake. Perhaps some of them will be interested enough in improving this skill that they will do some of the exercises and tests in the compiled list linked above.

June 2026 Writing Challenge

Sixteen years ago, my then-primary-partner now-best-ex was (and seemingly still is) a prolific writer of journal entries and short thought pieces. They used the website 750words.com to keep track of writing streaks and such, and I decided to join them for a month. The experience was somewhat formative for me, and led to me writing a lot more longer pieces over the intervening years. More recently, Inkhaven (http://inkhaven.blog) has sprung up as a yearly residency for writers, mostly in the rationalist sphere of influence, where everyone has to write a long form post every day for a month.

These two things, combined with many smaller influences, have motivated me to try for another solid month of writing. To celebrate my 44th birthday, I'll be writing and posting something long every day for the month of June 2026. I have a list of about twenty specific ideas so far, including topics like my coliving projects, interpersonal communication, court tactics, polyamory, and makerspaces. I'll probably include a few legal drafts as well since I've spit out a few of those every month for the last couple of years. Hopefully I'll have enough new ideas along the way to fill the rest of the month.

I'm hoping for a few different outcomes from this experience. I want to get back into the habit of writing long form posts. I want to expose people new to my social circles to my thoughts in a way I haven't really done in the last decade or so; I think the last time I knew a lot of people who were reading and responding to a lot of my long form posts was when I lived in Boston over a decade ago. I want to compare my old writings and see how I have changed, especially on a few of the days where I intend to explicitly revisit topics I already wrote about once or twice in the past. I want to distract myself from only ever doing legal drafting, which can be soul crushing work.

I don't know what standards I will hold the posts to, in terms of length or depth or time of day. Sometimes I end up writing 3000 words on a topic, and sometimes it's just 500. I don't think I want to feel compelled to expand 500 words to 750 or 1000 just to meet a target (basically how I wrote papers in high school and college). Maybe this will become clear to me in the first few days of this endeavor.

If you want to follow along, I'll be cross posting to https://sparr.substack.com, https://sparr.dreamwidth.org/, https://paper.wf/@sparr, https://facebook.com/sparr0, https://glosso.ink/u/sparr, and https://reddit.com/u/sparr, and I'll be posting links to one of those on https://twitter.com/sparr0, https://mastodon.social/@sparr, https://threads.com/@sparr0, and https://bsky.app/profile/sparr.bsky.social.

Post-Lawsuit Plans

For the last couple of years I have been in a perpetual state of “maybe everything wraps up next month”, with no money to put toward future plans, so I haven't been able to make any commitments or even confidently say where I would be when. That is starting to change now, with bigger junctures approaching in the various outstanding legal cases, including a trial date for the lawsuit preventing sale of my property. Today I'm making some predictions about likely outcomes and how things could shake out in the next year or two.

A. 10% chance I win my motion for summary judgment and can start to sell the property between April and June at market value. B. 10% chance I lose at trial and am forced to sell immediately in October at much less than market value. C. 70% chance I win at trial and can start to sell the property in October at market value. D. 10% chance I win at trial but the previous buyer continues to prevent a sale, such as through an appeal.

Outcome B is the worst plausible outcome. Their best settlement offer was about $500k, which would not be enough to settle my outstanding debts related to the property and events since the fire. If the court forces me to sell to them at that price, I would pay off as much as I could, keep 5-10% of the money, and use that to settle back in the Bay Area where I can get a job in tech again. Then it would take a year to pay off debts, and I could start from scratch on bigger plans.

Outcome D is the wild card, and would put me back in the state of having no idea when things will wrap up. However, my case load has recently dropped below one appearance per week, and that trend will likely continue, so by the time this outcome arrives I should have a reliable enough schedule and enough available mental capacity to go back to work regardless. I'd spend a few years working to pay people back before I could do anything big again.

Outcomes A and C are the exciting ones. As soon as I have a judgment lifting the Lis Pendens on the property, I can connect with other interested buyers and move quickly toward a contract and sale. Now that I've split the property into three separate parcels, each sale should be simpler and faster, and the parts worth more than the whole. I expect to close on those sales two to four months later.

If that comes to pass, then I will have a few months of notice that the sales will close between June 2026 and February 2027. I will make arrangements to pay off all of my debts, and take care of that in the days immediately following the first sale. I will have 45 days after the sales to identify the properties I am going to pursue next, and 180 days to buy one of them in order to defer a six figure capital gains tax.

That's not a lot of time to find and contract and close on the sorts of properties I'm pursuing. This is why I am constantly on the lookout for properties, keeping a list of likely candidates, discussing pros and cons, etc. I publish my best leads on the CoDwell Discord, and the most interesting ones to various social media platforms.

As soon as that ~9 month window opens (from case outcome to the end of the tax window), I need to get a lot of balls rolling all at once. Here's a prototype todo list for the first few months of that window, a lot of things I've done in the past but that have been on hold for a while now:

• Revive my CoDwell project.
• Reach out to everyone I know who has ever expressed interest in coliving or makerspaces or permaculture or anything adjacent to my project goals, as potential organizers, owners, investors, residents, participants, ...
• Start arranging trips to visit candidate properties like I did for the OR and MA properties in the past.
• Fill out dozens of govt and nonprofit grant and loan applications, especially USDA RD programs.
• Reach out to dozens of banks and other lenders to start moving toward financing for larger properties.

There will also be opportunities with less time and financial weight behind them. I'm starting to make plans for various events and trips and projects in mid to late 2026 and into 2027. It will be good to see people I haven't seen in far too long, polish some of the rust off various skills and hobbies, build some art, meet new people, etc.

As awful as the last two years have been, I am excited to see likely light at the end of the tunnel. If you'd like to talk about any of this, help me plan, point out problems with my expectations, etc, feel free to reach out. Otherwise, watch this space for updates as things progress.

Where I Want To Live

For years now people have been telling me that I should be trying to join an existing intentional community aligned with my goals and values, instead of or before trying to start my own again. I would actually love to be able to spend more of my time on things other than instigating and maintaining such a community. To that end, here’s a description of the environment in which I want to spend the next 5-20 years of my life:

• Many of us have an ownership stake, having dedicated significant effort and/or financial resources to the establishment and continued existence of the community and its physical presence.
• Most of us share at least most decision making authority about the direction of the community, within long term bounds which change much more slowly.
• We enforce our rules internally with low tolerance for community goals being derailed by misbehavior.
• We have a variety of large scale common amenities, particularly including well equipped workshop space, high ceiling and high seating capacity event spaces, acres of available land for growing food, and sporting or other recreational facilities.
• We prioritize enabling participants to earn a living using the common amenities, individually or in groups, such as by running home businesses or hosting paid educational events.
• We host a wide variety of events, including educational, artistic, camping, musical, and adult oriented activities, on weekly to yearly cadences.
• We share a significant amount of grocery purchasing and meal prep, and at least some common dining time.
• We regularly have friends and family visitors for hours to days at a time.
• We regularly cross pollinate with a major city event and social scene, either by being within convenient driving or transit distance or having frequent day and weekend trip carpools.

If you know of such a place and think I’d be a good fit, please point me in the right direction, or put me in touch with the right people. If not, I’ll keep trying to build it myself. Estate of Mind was a big step in the right direction, and CoDwell promises to be even closer to the mark. Most of you reading this will be welcome to join me in those future endeavors.

Good Riddance, 2025

I had thought that 2024 would be the worst year of my life for at least a while. Little did I know that it would lead to an even worse 2025. For posterity...

The Good

I've been living full time with my partner Mia, and it has been a healthy and beneficial relationship for both of us. My wife Victoria has found a musical companion and formed a touring duo, which seems to be making her happier than she has been in a long time. The holdout tenants at Estate of Mind are gone. It took a year and a half of eviction proceedings, hundreds of hours and thousands of dollars, and was a major achievement when it finally came to pass.

The Bad

I've been unemployed all year. I've made no money. Although I've still done some recreational software development to keep those skills sharp, my infrastructure skills are getting rusty. I'm another year behind on all of my debts. I owe commercial creditors tens of thousands of dollars which continues to mount, due both to interest and to my obligations to keep the utilities on for the tenants, and to a lesser degree to keep protecting the dorm building from winter. I owe friends (still, I hope?) hundreds of thousands of dollars that I borrowed to buy and attempt to repair this property. My divorce will be final in a few weeks. I miss Victoria, even though I know her new situation is better for her. I wish my plans to give her a space to perform and explore her passions hadn't gone so awry.

The Ugly

I'm still trapped at the Est8. The lawsuit preventing sale of the house is ongoing, and could stretch well into 2026. The damage to the manor is now almost entirely unrecoverable. Everyone who had hopes of restoring it has been scared off by the lawsuit, and I've long since run out of money to try to prevent further damage. I have a dozen ongoing court cases, across half a dozen courts in multiple cities. I was arrested for being at the courthouse at the same time as my ex-tenant who has a restraining order against me, when we were both there for a hearing with each other and for another case we were both connected to. The DA has been ignoring all of the video evidence showing I never approached or interacted with her, so it seems like this will go to trial, nine months later. The legal burdens have been extremely stressful and mentally taxing. I spent an average of two days a week in court and/or at the law library, and that's only down to one day now. Not even the holidays were a reprieve, with a dozen filings and deadlines in the last month, and a trial coming up next week. I fear that this experience has permanently impacted my mental stamina and stress tolerance.

Looking Ahead

Things are on track to improve this year. It will probably take months, maybe even most of the year, but I am hopeful that almost all of the problems above will be behind me by the time 2027 gets here. Maybe I'll even get to write a mid-year update with more positive news.

If you're out there reading my long form posts, feel free to get in touch. Some correspondence would be welcome. You surely know how to reach me if you found this.

Real Estate Lawsuit Situation

It has been 20 months since the fire that ended Estate of Mind and 11 months since the start of the lawsuit that is keeping me trapped on the property. There has been an uptick in inquiries about what's going on, so I'm writing this to bring everyone up to speed. If you know any attorneys who might be interested in taking this case on contingency, my offer is $100k from the sale of the property if the Lis Pendens is defeated, plus 30% of any recovered damages.

On March 1 2024, the manor suffered a fire which rendered it uninhabitable and beyond my ability to repair. We immediately stopped hosting events and recruiting new resident members, and over the next few months almost everyone living here moved out. I listed the property for sale and started arranging to move on with my life.

On June 14 2024, a buyer who had visited the property and made an offer signed a contract with me to buy the property. His name was Lee Jundanian, and he contracted to purchase the property under a Maryland LLC. The purchase price was $1,600,000, with him to pay half at closing and me to finance the other half with payments over the following five years. The contract called for a closing date of August 28 2024.

In June and July 2024, my employer let me know they were unhappy with my performance at work. I told them that the house fire situation was occupying my attention, and that I would be wrapping it up at the end of August so that I could focus on work again. In early September, when the sale hadn't closed as contracted and I was still distracted from work, I was fired. I have been out of work since then. I exhausted my unemployment insurance benefits in early 2025, and have had trouble finding a job that is compatible with the amount of time I have to spend on this situation and how often I have to be in court.

From August to November 2024, my agent and attorney and I grew increasingly insistent that he close the deal. He only ever responded with attempts to renegotiate the contract. Among other changes, he wanted to pay less, finance at lower interest, hold back far more money than we had previously agreed to deal with evicting the tenants, and make me responsible for damages caused by the tenants after closing. I attempted to negotiate a compromise position on some of these demands, but we never reached a new agreement. We finally asked him to formally terminate the contract and take back his deposit. He did not accept our requests.

On December 5 2024, he filed a lawsuit in Worcester County (Massachusetts) Superior Court, docket 2485CV01467. He asked the court to prevent me from selling the property to anyone else, to force me to sell it to him, and for damages. After a bit of legal wrangling, he recorded a Lis Pendens against the property, which effectively prevents me from selling to anyone while the lawsuit is pending.

At various points in 2025 I have invited him to close the deal as contracted. His latest offer to close the contract and settle the lawsuit is effectively that I give him a million dollar discount on the purchase price.

The crux of his case is that he claims I violated the contract first, and he seems to think that this means he can take as long as he wants to renegotiate. Here are his five accusations and my rebuttals:

“Seller has failed to make reasonable efforts to evict the remaining tenants residing at the Subject Property or to agree to an appropriate holdback.” I did make reasonable efforts to evict, and was still making those efforts at the time of the filing and until the evictions were complete. All of the tenants have been fully evicted for months now. We both agreed, in writing, to a holdback of $30,000. I wasn't required to agree to a holdback until the time of closing.

“Seller has failed to remove extensive amounts of trash and debris from the exterior of the Subject Property, as required by Section 12 of the Addendum.” Section 12 requires me to remove yard sale items specifically, which I did remove. We repeatedly discussed that the fire debris would not be removed, and it is not mentioned in the agreement or addendum.

“Seller has refused to close unless his unreasonable demands are met, including a demand that he be permitted to occupy the property for six months post-closing.” The context of this demand is that he was already refusing to close and making his own demands. I responded as negotiation. Specifically, I said that if he wanted to modify the contract to make me responsible for damages caused by the tenants after closing, he would have to let me stay to keep an eye on them.

“Upon information and belief, Seller has removed items from the Subject Property in violation of Section 5 of the Addendum.” He still hasn't specified what items this is referring to, including producing nothing about this during discovery, so it's difficult for me to respond specifically. I believe he is referring to windows, chandeliers, and other wood and glass elements that were stolen from the manor. I reported them stolen to Northbridge PD. In February 2025 most of them were recovered by Northbridge PD from one of my now-ex-tenants (Matthew Carr). Those thefts are the basis for at least one felony charge against him, a case currently underway in Uxbridge District Court.

“Upon information and belief, Seller has located another prospective buyer and, therefore, has intentionally failed and refused to transfer the property to Plaintiff in accordance with the terms of the P&S Agreement.” I did not refuse to transfer the property in accordance with the terms of the P&S Agreement, and have only failed to do so because he has refused to schedule a closing. I only started looking for other buyers months after this sale had failed to close as contracted.

My counterclaims demand the lifting of the Lis Pendens, for him to honor the contract, and for damages that I lower bounded as follows and expect to establish more specifically at trial: $7,000 per month interest on the contracted sale payment $5,000 per month interest on the contracted mortgage $10,000 per month decrease in value of the manor building due to water damage $100,000 decrease in value of the manor building due to freezing $12,000 per month in lost wages

Of course, this is just a summary that hits the major points of the situation. I've completely skipped the mortgage foreclosure, the tenant lawsuits, the mounting debt, actions by the town, the mental and physical toll, missed opportunities, etc. I could easily write ten times this much and not cover all the relevant information. Maybe I will, when this is all over.

Thank you for reading this far. I'm open to questions and discussion and advice. Dealing with this situation will continue to be my full time job until it's resolved or I find an attorney.

You might have heard that an eviction in Massachusetts takes 4-6 months. While this is technically an accurate average across all eviction proceedings, it's skewed by most cases settling within the first month or two, usually through mediation or payment. If a case goes to trial to have a tenant removed, it always takes 6+ months.

A tenant with no valid defense who loses every motion, hearing, and appeal can still delay the eviction repeatedly, sometimes a dozen times or more. Each delay adds weeks or months and they can add up to years.

Disclaimers:

1. This is not legal advice. If you need legal help, consult an attorney. Free legal aid is often available through volunteer lawyer programs.

2. While court records are public, collecting bulk data is difficult. This article is based on review of dozens of cases but does not represent every case or possible outcome.

3. Tenants should have fair legal protections, especially against unjust eviction attempts. Nothing here is intended to suggest otherwise.

Timeline of a Prolonged Eviction

This breakdown of the length of each step assumes the landlord acts quickly while the tenant asks for more time and appeals as often and long as possible.

Steps marked with ** delay the case regardless of the legitimacy of the case or the specific request, usually before it reaches a judge for consideration, sometimes based on law. Steps marked with * only delay the case if a judge allows it. Unmarked steps are mostly mandatory once the process has gotten that far.

Phase 1: Before Mandatory Mediation (2-4 Months)

• [14-62 days] Landlord serves the notice to quit and waits the required period.

• [1-2 weeks] Sheriff serves court papers then Landlord files the case.

• [30-60 days] Clerk schedules a “first tier event” with mandatory mediation.

Phase 2: From Mediation to Trial and Ruling (1-14 months)

• **[1-3 weeks] Tenant requests extra time to file an answer.

• *[0-4 weeks] Judge may grant the request.

• **[1-2 months] Tenant applies for rental assistance, pausing the case. Ignoring deadlines or submitting incorrect information can delay the application.

• *[0-4 months] Tenant applies for rental assistance repeatedly until a judge stops accepting the delays.

If rental assistance is approved for less than is owed, the landlord will be required to forgive the excess to receive any payment. If they receive payment, they will have to restart the eviction process from the beginning for continued non-payment.

• **[1-3 weeks] Tenant requests additional time for discovery.

• *[0-8 weeks] Judge may grant the request.

• **[1-3 weeks] Tenant requests additional time for the pre-trial process.

• *[0-8 weeks] Judge may grant the request.

• *[0-6 weeks] Judge usually reschedules the jury trial as a bench trial if the tenant has still failed to follow the earlier processes.

• [1 day] The actual trial, whether jury or bench, will usually take less than one full day in court, but...

• [0-6+ weeks] Judge may take the case under advisement indefinitely.

From Ruling to Docketing of Appeal (1-7 months)

• [0-1 month] Judge may include a delay before entry of judgment.

• **[10 days] Tenant waits to file their notice of appeal.

• **[1-3 weeks] Tenant asks the judge to reconsider their decision.

• *[0 or 10 days] Judge may change their decision.

• **[1-3 weeks] Tenant asks the judge to change a specific detail of their decision.

• *[0 or 10 days] Judge may change their decision.

• Tenant files the notice of appeal.

• **[1-3 weeks] Tenant asks to waive the appeal bond.

• **[2-3 weeks] Tenant appeals the appeal bond waiver decision.

• **[1-3 weeks] Tenant asks to waive the cost of transcripts.

• **[2 weeks] Tenant waits before ordering transcripts.

• [1 week] Transcriber creates and sends transcripts to the parties and court.

• [1-3 weeks] Clerk “assembles the record” of case details for the appeal court.

• **[2 weeks] Tenant waits to docket the case with the appeal court.

Landlord may be able to shortcut some of the transcript steps by ordering the transcript(s) in advance, usually for hundreds of dollars.

Appeals Court (7-15+ months)

• **[40 days] Tenant waits to file their brief.

• **[1-3 weeks] Tenant asks to extend the deadline.

• *[0-3 months] Judge may allow extending the deadline.

• [0-30 days] Landlord files their brief.

• **[14 days] Tenant waits to file a reply.

• **[1-3 weeks] Tenant asks to extend the deadline.

• *[0-3 months] Judge may allow extending the deadline.

• [4-9+ months] Appeals court makes a decision, possibly after scheduling oral arguments.

Supreme Judicial Court (??)

There is much less data available about eviction case processes and outcomes in the SJC. I haven't found enough examples to confidently propose timeframes for this phase.

Execution (2+ months)

• [1-2 weeks] Landlord applies for execution of the eviction.

• [1-2 months] Sheriff schedules the execution.

• Tenant requests a stay of execution.

• *[1+ months] The judge may grant the request. Sometimes repeatedly.

• [1 day] Sheriff escorts the tenant off the property.

Civil Orders and Judgments

Some parts of the eviction case will usually result in an order that the tenant pay overdue and/or ongoing rent. The landlord might also file a civil case for unpaid rent or other costs and damages. Most eviction defendants are “judgment-proof”. Even with court orders for payment, landlords usually never recover unpaid rent.

Potential Partial Solutions

Here are some specific changes to the current process that could reduce the impact of the delaying tactics described above.

Disallow Consecutive Delays

Multiple motions or requests in the same phase of the case should be heard at the same time and only delay the case once. e.g. A single delay between mediation and trial for more time to file an answer, participate in discovery, draft a pre-trial memorandum, and/or pursue rental assistance. Ditto for the requests to waive appeal bond and to waive transcript costs. Ditto for the notice of appeal, motion to reconsider, motion to amend, etc.

Speed Up Scheduling

Housing Court is supposed to be faster than other courts, yet many motion hearings are scheduled 2-3 weeks out, sometimes as much as 8 weeks. When things go faster in Superior Court than Housing Court, something is probably amiss.

Single Justice Appeals

Eviction appeals could be handled by the Single Justice session of the Appeals Court, with a higher bar for basis and bond for further appeal to a panel.

Shorter Timelines

This is surely my most politically charged suggestion. While I agree that states with 1 week evictions are unreasonable, I think our year or longer is just as bad.

• From eviction notice to case filing should be 1 month at most, not 2.
• Mediation should be scheduled and notice served as the same time as the case filing. It should be 1-3 weeks out like any other notified hearing, not 1-2 months plus 1-2 weeks.
• Rental assistance application should be a single 1 month delay.
• If non-payment continues after rental assistance, the case should pick back up with no delay, not restart.
• Tenants should have days, not weeks, to take steps like ordering transcripts.
• Removing the tenant after the final day in court should take days, not months.

Legal Improvements

While I'm at it, here are a few places I think the eviction process and adjacent matters should be more explicitly defined by law, rather than subject to the non-binding opinions of hundreds of different judges. These are, admittedly, more tied to my personal experience than the rest of the article.

• Required contents of a notice to quit. It could even be a standard form, with instructions.
• Consequences for violating a court order to pay rent while an eviction case is ongoing.
• The process for enforcing lease rules regarding losing access to parts of the property, e.g. “If you poop in the pool then you can't use the pool any more”.

Author

Thanks for reading this far. My name is Clarence Risher and my friends call me Sparr. As I write this, I am about 10 months into two prolonged evictions in MA in the only home I've ever owned, which have prevented me from selling the property. It's a complex situation, but most of the complexity isn't really relevant to the evictions. I've reached the Appeal Bond Waiver Appeal step once and been through the earlier steps a few times. I anticipate at least 9 more months of delays.

I don't expect this article to make a difference soon enough to affect my own cases. I know that some tenants might use this as a guide to abuse the system. My goal here is to raise awareness of the problems in an attempt to motivate the legislature and courts to make this process more just and fair.

I can be reached at [email protected] if you have questions about my personal experience or any of the more general things I've written about here. I am also open to hearing new information that I may have overlooked or misunderstood when writing this article.

Here's an update on the state of various major situations affecting my life.

The Estate of Mind intentional community coliving project ended late last year. I tried to find a way for some subset of the community members to stick together in the dorm and pine house, operating on a smaller scale after the loss of the manor. Unfortunately all the ideas we pursued didn't pan out and almost everyone moved on to the next part of their life in the months after the fire.

There are two tenants still living in the dorm, Lisa Pepin and Matthew Carr. I am 9-11 months into the processes of evicting them, with 75% confidence I'll have them out 2-8 months from now. For context, the average length of an eviction in MA is 4-6 months without an appeal or delaying tactics. There are also up to half a dozen 2-6 week delays available, and an appeal automatically adds an additional 2+ months, both regardless of merit. They have declined offers including $5-30k in cash, moving expenses, and/or vehicles, from myself and from interested buyers of the property. They are collectively about $17k behind on what they owe me, about $8k of which they are already under court order to repay. I am currently legally required to provide utilities including heat to a 15 bedroom building for the two of them, as well as to continue maintaining the whole building including vacant bedrooms and private bathrooms. I am far behind on those costs, and they far exceed my income. Matthew's eviction has gotten to a judgment and past the reconsideration delays, and now we're going into the appeal process. With Lisa, I got a default judgment when she didn't show up for trial after giving the court short notice of a doctor's appointment, then she got another judge to undo that decision, and then when we finally got to trial a second time the judge noted that I didn't put her bedroom number (the one effectively destroyed by the fire) on the eviction notice so he was dismissing the case and I had to start all over. That second attempt is currently at the early stage where she gets ~45 days to prepare for a mandatory mediation session.

My attempts to sell the property have been stymied a few different ways. First by the manor fire and nature of the property. I was able to resolve that somewhat effectively by subdividing the property so the value proposition of each piece is much more straightforward, and this attracted multiple offers in a very short span once the new listings went up. Second, the presence of non-paying tenants who refuse to leave. I'm working on that in housing court as described above. Third…

A man named Lee Jundanian has brought a civil suit against me to force me to sell him the property and prevent me from selling it to anyone else. He's also demanding what might be hundreds of thousands of dollars in damages. We had a contract for him to buy the property, a sale that was due to close in August of 2024. He has refused to close ever since then, only responding with new attempts to renegotiate the contract. In the fall of 2024, his outstanding contract scared my agent away from accepting new offers or re-listing the property. Now his lawsuit means that no title insurance company will insure a sale, so no mortgage company will lend on it. While a pure cash buyer with a tolerance for legal risk could still buy part or all of the property, that is unlikely. I was a week from closing one sale and two months from closing another when he locked the property up, and those deals are now falling through. I am pursuing a few legal strategies that have some chance of unlocking the property in ~1 or ~9 months, but more likely I will need to endure 18+ months to the end of that trial before I can get a judge to terminate that contract. The faint bright spot at the end of that long tunnel is that I am counterclaiming against him for my own hundreds of thousands of dollars in damages, which increase every month the trial goes on. I may have to doubly break the corporate veil to effectively collect on a judgement of that size, which would take additional years.

The second time I found that one of the tenants (Lisa) had moved into someone else's bedroom without permission or even telling anyone, and with the local police declining to “get involved in a civil matter”, I physically removed her from the room. This allowed her to get a restraining order against me. This has made it difficult for me to manage the property; now I'm having to hire people to do simple things in the dormitory, and next week I'm going to have to spend $400 to hire a cop to escort me in so I can meet a health inspector. I'm pretty sure the part of the domestic violence law that led to the order is a violation of the MA constitution; there's no way I have less right to defend my property from trespass just because I live there. I'm appealing that order, but the courts are letting her delay that process by months as well. There's a chance the order will expire before the whole appeal process finishes, but I'll still see it through regardless.

If you're local and want me out of town, the fastest way to make that happen would be to help resolve one of the problems described above so that I can leave sooner. If you just want excuses to keep complaining, feel free to sit back and enjoy the show.

I lost my job in September of last year. I was spending too much time dealing with problems at home, and when the sale failed to close in August I wasn't able to keep my commitments to put more time into work. It took about two months to get approved for unemployment benefits, during which time I also couldn't get approved for other public benefits, so that was a really tough time. I have about 10 weeks of unemployment benefits left now, so those tough times are on the horizon again. The effort and stress for everything going on has made it infeasible for me to take on new full time work, so I've mostly been pursuing gigs that haven't panned out. Fortunately I'm finally making some headway on interviews for a “real job”, and there's a decent chance I'll find work in the next couple of months. It's going to take a very rapid transition to turn money from a new job into an ability to stop spending all my time on the problems here at home; fortunately just a couple of paychecks will be enough to retain an attorney for the civil lawsuit, and less than that would hire one for the evictions.

I've also been working on re-launching my CoDwell project, which was one of my efforts to acquire property for a large coliving intentional community before I succeeded with the est8. There's a lot more details on that on the project website at http://CoDwell.org. The short version is that I want to buy an old boarding school near Portland OR and have 5-10 intentional community groups with different focuses (permaculture, maker, coparent/homeschool, etc) all share the property and use its amenities. I'm going to be spending the next 6-12 months finding people and money to try that project idea again.

As soon as I can disentangle myself even partially from the property in MA, I'll be headed west. Maybe a short or long road trip. Maybe aiming for Portland or SF initially or for a while. Lots of variables there. Get in touch if you want updates on more personal matters like health, family, relationships, work, etc. Especially if have novel ideas related to anything above. Otherwise, I hope to have more time in the coming year to visit and catch up with friends and acquaintances.