Three out of four homeowners never do this one thing

Today's Tip: Fighting your property tax assessment

Three out of four homeowners have never appealed their property tax bill… and most of them do not even know they are allowed to.

Let me explain…

A survey from the property tax firm Ownwell earlier this year found that 74 percent of American homeowners have never once filed an appeal on their assessment. More than half did not know it was an option.

Meanwhile, counties all over the country are in the middle of reassessments right now. Lancaster County, Pennsylvania mailed out fresh 2027 valuations in June. New Castle County, Delaware went through a bruising round of its own. The letters land, the number is bigger than last year, and most people just… pay it.

I want to tell you about my neighbor Ingrid.

Ingrid is 66, semi-retired from a long career as a dental hygienist, still fills in two mornings a week at a clinic downtown. She lives in the same tidy little three-bedroom in Rochester, Minnesota that she and her late husband bought in 1994.

Last week she got her reassessment notice in the mail. Her home's assessed value had jumped considerably from the year before. She called me, frustrated, and asked if there was anything she could do.

There was. And it took less than an hour, sitting at her kitchen table with a laptop and a cup of coffee.

We used Claude. We uploaded a photo of her assessment notice, a photo of the sale prices of three houses on her street that had sold in the last twelve months, and a short list of things that were wrong or outdated on the county's record for her house.

Then we asked Claude to write her a formal appeal letter she could sign and mail.

Here's the prompt that does it…

Claude drafted the letter in about twenty seconds. Two paragraphs, tight and calm. A numbered list of the three comparable sales. A specific request for the review hearing that Olmsted County offers.

Ingrid read it over. She changed one sentence to sound more like her. She printed it, signed it, and dropped it in the mail the next morning.

Now, I do not know yet how her appeal will land. That is a question for the assessor's office, not for me.

But here is what I do know. Ingrid did the thing that 74 out of 100 homeowners never do. She made her case in writing, on time, with evidence. That alone puts her ahead of almost everyone in her tax bracket.

I know what some of you are thinking… "But I do not know what the comparable sales are on my street. I would not know where to start."

You start with the county's own website. Most county assessor sites let you look up recent sales by street or by neighborhood, for free. Zillow and Redfin also list sale prices going back a year or more. Pick three homes as close to yours as possible in size, age, and layout, and write down the addresses and sale prices. That is the file you upload with your assessment notice.

If you got a reassessment notice this year and something about the number felt off, do not shrug and pay it. Pull the notice out of the drawer, take a picture of it, and spend an hour with Claude and a cup of coffee.

You do not have to win the appeal to make it worth doing… you just have to file it.

Ingrid mailed hers on a Tuesday.

★ Quick Wins

Skill Builder: Teaching AI to sound like you

Here is a small skill that changes everything about how you use Claude. Or Gemini. Or Grok.

Instead of asking the AI to guess how you write, you teach it. You paste in a few examples of your own writing and you tell it what you like and what you do not. From then on, everything it drafts for you comes out closer to what you would have written yourself.

The reason this matters is that generic AI writing sounds like generic AI writing. It uses phrases you would never use. It is too formal, or too breezy, or sprinkled with words that make your daughter squint and say, "Mom, did you write this?" A style memo fixes that. You write it once, save it, and paste it at the top of any drafting request.

Here is what to put in yours…

Save the style memo somewhere easy to find. A note on your phone works. Then next time you ask Claude to help you draft anything, paste the memo at the top and add your request underneath.

After a while you will notice something. The drafts start needing fewer edits. Your voice comes through. That is not a small thing when you are writing an appeal letter or a note to your grandchildren or a message to a doctor.