Prepare and file a property tax grievance on deadline day, between meetings, with Claude Cowork (partial)
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- by Wes Pomeroy (Substack)
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What went wrong: The grievance was filed on time; the post doesn't report the result.
Outcome
Wes Pomeroy's town assessment had nearly doubled since they bought the house eight or nine years earlier, and they realised the last day to challenge it was that day. Using Claude Cowork connected to Gmail, Google Drive and Chrome, they first asked about the official rules and deadline, which turned up that a mailed form wouldn't count: it had to be handed in in person by 9 PM. Claude found an old broker appraisal, the assessor's email about a renovation and the addition's square footage, and cut a weak argument about crime risk that had no data behind it. It filled the official form, drafted a cover letter, built a comparison page and a labelled photo exhibit and merged them into one file. Pomeroy says the first pass was about 65% right and corrected it several times. Both owners signed and the packet was stamped at the assessor's office before the deadline. The post doesn't give a result yet.
Agent
Prompt Original prompt
Exact prompt as published in the source.
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.
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Optional stronger version
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Before you start, ask me 1–3 short questions about anything important that's missing below. Keep them quick. Then do the task, checking in with me at the key points. Goal: Prepare a complete property tax challenge before the deadline, using evidence I already have. What I can give you (ask for whatever's missing): - My address and the assessor's or town's website: [DETAILS] - Where my documents are (email, drive, photos): [DETAILS] - The value I think is fair and why: [DETAILS] You're not my accountant or financial adviser. Show your working, label estimates as estimates, and tell me which points a professional or the official source should confirm. Rules: - Start with the official rules: which form, how it must be submitted, and the exact deadline, from the assessor's own site. - Search my email and files for appraisals, assessor letters and measurements, and show me what you found. - Tell me which of my arguments are strong and which are weak, and why. - Fill in the official form, draft a cover letter, and build a one-page comparison with similar homes. - Show me every page before it's final. - Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify. - Add a plain next-steps sheet: who signs, how many copies, where to hand it in and what proof to keep. Output: A print-ready packet and a short list of next steps for submitting it. You'll know it worked when: the packet is filed on time and accepted. Before you finish: re-read my goal and constraints, check your answer against each one, and list anything you assumed or couldn't confirm.
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Your prompt
Before you start, ask me 1–3 short questions about anything important that's missing below. Keep them quick. Then do the task, checking in with me at the key points. Goal: Prepare a complete property tax challenge before the deadline, using evidence I already have. What I can give you (ask for whatever's missing): - My address and the assessor's or town's website: [DETAILS] - Where my documents are (email, drive, photos): [DETAILS] - The value I think is fair and why: [DETAILS] You're not my accountant or financial adviser. Show your working, label estimates as estimates, and tell me which points a professional or the official source should confirm. Rules: - Start with the official rules: which form, how it must be submitted, and the exact deadline, from the assessor's own site. - Search my email and files for appraisals, assessor letters and measurements, and show me what you found. - Tell me which of my arguments are strong and which are weak, and why. - Fill in the official form, draft a cover letter, and build a one-page comparison with similar homes. - Show me every page before it's final. - Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify. - Add a plain next-steps sheet: who signs, how many copies, where to hand it in and what proof to keep. Output: A print-ready packet and a short list of next steps for submitting it. You'll know it worked when: the packet is filed on time and accepted. Before you finish: re-read my goal and constraints, check your answer against each one, and list anything you assumed or couldn't confirm.
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Source
https://wespomeroy.substack.com/p/property-tax-grievance
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