I Used AI to Fight My Property Taxes

Most of what gets said about AI right now is intangible. Especially in business - it's all potential and disruption and what-it-all-means, hovering a few thousand feet up, never touching the ground where the work happens. People read it and get it well enough - the way you get economics. It connects to your life, it's interesting, and it never quite turns into something you can do on Monday.

So I'm going to try something here, and keep at it: walk through real things I've used AI for. Not a demo, not a feature list - a real problem I had, the steps I took, and the thinking under each one. Something you could pick up and use on a problem of your own.

This first one is about my property taxes.

The problem

This year the town's assessment of our house landed well above what we think it would sell for. We bought it eight or nine years ago - admittedly below market. A great and much-needed deal at the time, the one that let us stay in the town we loved. Since then, the assessed value has nearly doubled. We did one modest renovation; otherwise the house is the house, the town is the town, the schools are the schools. What changed was the market, and the assessment rode it up. We're planning to stay, not sell, so none of that paper appreciation does a thing for us except raise the bill.

This isn't a hardship story; we're fine. But an assessment is supposed to track what a house is worth, and when it drifts above that, the bill is wrong - and we're not the only ones who pay for it. Our neighbors' assessments move with ours. People on fixed incomes, in a town that used to be a lot more blue-collar, are the ones it can squeeze out. You don't have to feel for our situation to see the principle: anyone, for any reason, can end up paying on a number that isn't true. This is about how you actually use AI to try to get it back to something fair.

The real constraint

There's a short window each year to formally challenge your assessment, and I'd let it sneak up on me. I finally sat down to do it today, only to realize that the last day to file it - is today.

It wasn't even a busy day. I had some work to get through - a couple of meetings, the usual email - but nothing brutal. Just enough that I couldn't clear a block to sit and grind through this in one go. So I did it in pieces, a stretch here and a few minutes there, around everything else.

Done by hand, this is hours of unbroken work: reading the rules, digging up evidence, filling out a government form, writing a cover letter, assembling the whole package. Hours I didn't have, and couldn't have spent in one sitting anyway. That constraint - not much time, and none of it continuous - is the situation most people are in. Deadlines creep up. Life's full. You fit the important thing into the gaps, usually at "good enough" quality, and usually running yourself down to do it.

What you'll need

Before we start, let's lay out our materials. Nothing exotic - if you've got these, you can do everything below.

Claude Cowork, on a paid plan. It's the version that can do things for you - open files, fill out forms, use the web - not just talk.
Your Gmail connected, so it can find things buried in your inbox.
Your Google Drive connected, so it can reach your files and photos.
Chrome connected, so it can read live web pages: official rules, listings, public records.

That's the whole kit. Now let's work.

Research

We start by getting the 101 on the process - what we're looking at. For something like a grievance, the rules decide what flies and what doesn't, and they're easy to get wrong. So before anything about the house, we ask:

"What do I file to challenge this, in what form, by what means, and by when?"
"Check the town assessor's official site for the rules and the deadline - not a forum, not a guess."
"Find recent sale prices for comparable homes nearby."
"Pull the property's assessment history."

When I did this, the rules check turned up the thing that would have sunk me: a mailed form doesn't count - it has to be received in person by 9 PM. Get the process facts before anything else.

Pull in what you already have

Most of what you need to make your case, you already have - you've just forgotten where it is. So before building anything from scratch, we point Claude at our own accounts and let it dig:

"Search my email for the appraisal a broker did for us a while back."
"Find the email from the assessor's office about our renovation."
"Pull the square footage of the addition from my architect's note."
"Grab the photos I took today from my Google Drive."

It found all of it. You're probably sitting on more evidence than you think - let it do the digging.

Talk it through

You'll have a stack of reasons your number is wrong. Some are good. Some will hurt you. This is where Claude earns its keep - as a second opinion that's willing to tell you no. So we lay them all out and ask:

- "Here are all my arguments. Which ones really help, and which make me look like I'm reaching?"

It cut a weak one - a hunch about crime risk near the highway, with no data behind it - and said why. It kept the strong ones and told me what each needed to land: a photo here, a comparable sale there. A tool that only ever agrees with you isn't helping. The useful part is when it tells you a piece of your case is weak.

Build it

Once you know your case, you hand off the assembly. This is the part that eats hours by hand - and the part you can set going and step away from, which is how it fit around a normal day. We ask for the pieces, one at a time:

"Fill out the official form with our details and the value we're claiming."
"Draft a cover letter that makes the case."
"Build a one-page, side-by-side comparison of our house and the comparable."
"Turn my photos into a labeled exhibit."
"Merge it all into one print-ready file."

When the thinking's done, the production - filling, drafting, formatting, assembling - is exactly what to hand off.

Check the work

Everything above gets you a draft. This part - all you - is what turns that draft into something you'd actually file. An AI's first pass is never the final one. In my experience it lands around 65%, even when you've fed it a pile of context up front. It reads like it's done. It isn't.

So you review everything, and the higher the stakes, the harder you look - line by line, claim by claim. When something's wrong, you don't just say "fix it." You say exactly what's wrong:

"That photo isn't the wall - it's just junk in the yard. Drop it."
"This shot is the highway ramp behind the house. Relabel it."
"You used my work number. Here's my cell."

Then you check the revision. Then you check that. You keep going until it's right - not "good enough," but right. This is where the gaps-in-your-day problem flips in your favor: making it fix a thing and re-check its own work costs you almost nothing, so there's no reason to settle. Each pass, it made the correction and verified again - but I was the one who decided what "right" meant.

You own the facts and the standard; it owns the redrafting. Whatever else you do, don't ship the first draft.

The last mile

When it finally hit 100%, it added something I hadn't asked for: a plain next-steps sheet. Print, both owners sign, make two copies, hand it in, get it stamped.

So that's what we did. I sent the finished packet to my wife at work; she printed two copies and signed them. I picked them up, signed them myself, drove it over to the assessor's office, handed it in, and got my copy stamped. The woman at the counter looked it over and was visibly impressed. We got to talking, about music of all things, for a good five minutes. It was one of the best parts of my day.

Your turn

None of this works with an AI that can only talk back to you. What made it work was that it could reach into my world and do the things above - find the email, read the PDF, work the public-records site, build the documents - all while asking before it touched anything that mattered.

So here's the whole thing on a platter. Go get Claude Cowork, connect your accounts, and give it the kind of instructions you saw above. Then work the way we just worked: get the 101 on how it works, pull in what you already have, talk through what's strong and what's weak, build the pieces, and then check, and check, and check until it's right. That last part stays yours - you're the source of truth from start to finish. The machine does the work; you decide what "done" means.

You don't have to be a developer. You can do this, and it's real - I did all of it today, between meetings, and had a stamped packet filed before the deadline.

So look at your own life. The thing you keep putting off because it's a slog - the claim, the application, the dispute, the filing, the research you never get a clean afternoon for. Break it into its parts: what's the research, what do you already have, what needs a second opinion, what needs building, what needs checking. Hand off the parts you can. Stay the source of truth on the rest. That's the move. Pick the thing you've been dreading, and try it.