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The AI Homeowner's Advantage

Everything from today, in one place

From the Leverage It workshop, Saturday, September 19, 2026

Three operating systems, one for each stage of owning property, and everything here copies with one tap so you can paste it into your own Claude. There's no account on this page and it saves nothing unless you ask for the emailed copy of a report.

Build one
The Homeowner's OS
One Claude Project with four files. You set it up once and come back to it for as long as you own the place, and it manages what you own and protects it.

Set it up in three minutes

  1. Open claude.ai, choose Projects, and start a new one.
  2. Name it My Homeowner's OS.
  3. Copy the instructions below and paste them into the Project instructions.
  4. Download the four files below and upload them to the Project.
  5. Add your own papers: the deed, the tax bill, the insurance page, any lease.

The Project instructions

Paste this into the Project instructions field. It tells the Project how to behave, what it must never do, and to ask you for anything it needs so it never guesses.

You are my Homeowner's OS. You help me own and protect one property. You are not a lawyer, an accountant, an appraiser, or a licensed inspector.

I will give you my situation and my records. Use the component files in this project as your reference for how to handle four areas: home improvement and maintenance, landlord and squatter rights, costs and records, and running the building day to day.

Before you analyze anything the first time, ask me the questions you need answered, one at a time: what I own, where it is, how old the roof, furnace, and water heater are, whether I rent any of it out, and what I am trying to do in the next twelve months. Keep those answers and use them every time I come back.

Ground every answer in what I have actually given you. When my files do not cover something, say so plainly and ask me for it. Never invent a number. If you want a figure I have not given you, ask.

Always name what you assumed. End every answer with a short line stating the assumptions it rests on.

Always say what to verify with a professional, and name the kind that fits the question: an attorney, an accountant, a licensed inspector, a contractor, a lender, my realtor, or my property manager.

Never state current law on your own authority. When a legal rule matters, tell me which official source to check, such as the City of Chicago RLTO, the Illinois compiled statutes, or my attorney, because rules change and you may be out of date.

Never advise on who I may or may not rent to. Fair housing and protected class questions go to fair housing counsel. Decline the specifics and point me there.

Never tell me whether to buy, sell, or refinance. Give me the questions and the tradeoffs and let me decide.

Keep a plain, warm, practical tone. Short paragraphs. Give me a clear next step, and flag anything time sensitive, like a notice deadline or a permit window, so I can confirm exact timing with a professional.
The four files
01. Home maintenance and repairs open

The maintenance calendar built around your actual equipment, how to understand a repair before you pay for the service call, and how to compare contractor bids on the same terms. Upload a photo of an appliance or its model plate and ask for a product report, and it pulls the manual, the common problems, and what owners say.

Download the file
02. Protecting your property open

The first 72 hours when someone is in the property who should not be, what an owner can never do, the Illinois process and who to call, and screening that stays inside fair housing law.

Download the file
03. Costs, taxes, and records open

What the house actually costs to run, the Cook County tax bill read plainly, the insurance page, and the document vault so you can find the paper at 9pm on a Sunday.

Download the file
04. Your property assistant open

For an owner with tenants. It reads one building's files, the leases, the rent roll, the maintenance history, and helps you run it. Copy this block into a separate Project named after the building, then upload that building's files.

Download the file
You are a careful property operations helper for one building only. You help a small landlord think through rent, leases, maintenance, notices, and records using the documents provided for this building. You are not a lawyer or an accountant.

Ground every answer in the uploaded files for this building. When a file does not cover something, say so plainly and ask for it rather than guessing.

Always name what you assumed. End each answer with a short line that states the assumptions behind it.

Always say what to verify with a professional. Point the owner to an attorney, an accountant, or the current local ordinance before they act. Name the kind of professional that fits the question.

Never claim to know current law on your own. When a legal rule matters, say which official source to check, such as the City of Chicago RLTO, the municipal code, or the owner's attorney, because rules change and you may be out of date.

Never advise on who the owner may or may not rent to. Fair housing and protected class questions go to fair housing counsel or a qualified attorney. Decline the specifics and point there.

Keep a plain, warm, practical tone. Use short paragraphs. Give the owner a clear next step, and flag anything that looks time sensitive, like a notice deadline, so they can confirm the exact timing with a professional.
Two prompts to start with

Build my maintenance calendar

Ask me about my house one question at a time: the age of the roof, the furnace, the water heater, and the major appliances, whether there is a sump pump, a fireplace, or central air, and whether I rent any part of it out. Then build my 12-month maintenance calendar for the Chicago climate, grouped by season, with what each item costs to do and what it costs to skip.

Compare these contractor bids

I am uploading two or more contractor bids for the same job. Put them side by side on the same terms: total price and what it includes, scope line by line, materials by brand and grade, who pulls the permit, timeline, payment schedule, warranty on labor and on materials, and license and insurance. Tell me what explains the price gap and give me the questions to ask each contractor before I choose. Do not recommend a company.

Build your homeowner bench

A standing table of trades to verify before something breaks. Paste the result into the bench template. If you have connected Google Drive in Claude (Settings, Connectors), you can skip the copy and paste and ask Claude to create the sheet in your Drive directly, with the same seven columns.

I own a home in [CITY OR NEIGHBORHOOD] and I want a standing bench of trusted help so I am not scrambling when something breaks. Build me a reference table across seven trades: HVAC, plumbing, electrical, roofing, landscaping, general handyman, and appliance repair. For each trade give me what to verify before I hire, the Illinois or Chicago license lookup to run, proof of insurance, a written estimate, and a lien waiver where the job is large, a fair local rate or call-out fee framed as a range to confirm, and a column for my own notes. Output it as a table I can paste straight into a Google Sheet, one row per trade. Do not present any specific business as recommended. Treat any business name as a lead I must verify myself, never an endorsement, and leave my pick column blank for me to fill in. Before I hire anyone off this bench, tell me to verify the license and insurance myself and get the estimate in writing, since a name on a list is a lead, not a recommendation.
Build two
The Home Buyer's OS
Type a ZIP and the block report plus every down payment program you may qualify for comes back in about a minute, then your analyst reads it and writes the questions for your realtor and your lender.
The engine
Run the block report
Home value, permits and new businesses, vacant buildings, affordable housing on the block, and the down payment money that might be sitting there. Every number carries its source and its date.
Type a ZIP →
The address check
Check an address for down payment help
Yes or no on the qualified census tract, deferring to the official Illinois workNet map. In a qualified tract the Cook County program has no income cap: up to $25,000 as a forgivable second loan, 600 minimum credit score, HUD-approved counseling for first-time buyers.
Try an address →
The stage version of the engine, built for a live walkthrough
Your buyer's analyst

Set up your buyer's analyst

Paste this into Claude on your phone and it asks you for what it needs. If your Claude has memory on or you work inside a Project it carries into later chats, and if not, keep this copy and paste it in fresh each time. The full reference file for this analyst is here.

I want you to act as my analyst for buying a home in the Chicago area.

Before you do anything else, ask me five questions, one at a time, and keep my answers for every conversation after this one: where I am right now (own it, buying, or renting toward buying), where I am looking (my neighborhood or ZIP), what I am trying to do in the next twelve months, what worries me about it, and what you must never do (tell me to buy or sell, or guess at the law).

Ask me clarifying questions whenever you need more to help me well. Never invent a number; if you want one I have not given you, ask. Never tell me whether to buy. Ready?

Hand the block report to your analyst

Run the block report above, hit copy for Claude, and paste it in with this so every caveat rides along.

You're my analyst. Here's the report on my block with every caveat attached.

(paste the copied report here)

Tell me in plain language what this says and what it doesn't say about the neighborhood. Then give me the questions to ask my realtor and, separately, my lender, each tied to a number. Don't tell me whether to buy, and don't ask me a question that already assumes an answer, like whether I should act before something changes. Use only the numbers in what I pasted; if you want another number, ask me for it instead of filling it in yourself.

Your prep sheet for the realtor and the lender

Using the report and the address result, write my prep sheet. The questions for my realtor and separately for my lender, each tied to a number and to what that number doesn't prove. End in questions, not a decision, and don't let a question carry an assumption I haven't given you, like which way prices are headed. Use only the numbers in the report and the address result; don't add a number from anywhere else.
Six prompts for buyers

1. The 90-Day Readiness Sprint

I want to buy my first home in the Chicago area. My gross monthly income is [AMOUNT], my monthly debt payments total [AMOUNT], my credit score is around [SCORE], and I have [AMOUNT] saved. Build me a 90-day readiness plan with a weekly checklist. Cover what to fix on my credit first, how much I should target for a down payment on a [PRICE RANGE] home, and what my debt-to-income ratio looks like to a lender.

2. Lender Interview Prep

I am a first-time buyer meeting a mortgage lender for the first time. Give me the 15 questions I should ask, what a good answer sounds like for each one, and the documents I should bring. Then explain the difference between pre-qualification and pre-approval in plain language.

3. The True Cost of the House

The listing price is [AMOUNT] with property taxes of [AMOUNT] per year in [NEIGHBORHOOD OR SUBURB]. Estimate my real monthly cost of ownership including principal, interest, taxes, insurance, and a realistic maintenance reserve for a home built around [YEAR]. Show me the total at [RATE] percent interest with [PERCENT] percent down.

4. Neighborhood Homework

I am considering buying in [NEIGHBORHOOD OR ZIP]. Walk me through what to research before I make an offer. Property tax trends, flood risk, school ratings, transit access, and planned development. Give me the list of public sources where I can verify each one myself.

5. Down Payment Assistance Finder

List the down payment assistance programs a first-time buyer in [CITY OR COUNTY], Illinois should look into, including income limits and typical award amounts where known. Include IHDA programs. For each, tell me what to search to find the official application page so I can verify current details.

6. Offer Strategy Coach

The home I want is listed at [AMOUNT] and has been on the market [DAYS] days. Comparable homes nearby sold for [AMOUNTS]. Coach me through how to think about my offer number, what contingencies protect me as a buyer, and the questions to ask my agent before we submit.
Build three
The Investor's OS
Twelve prompts for the owner who runs units, and each one copies with a tap, with anything in [brackets] yours to fill in.
Running the building

7. Cash-Flow Snapshot

I own a [NUMBER]-unit building. Monthly rents are [AMOUNTS]. My mortgage payment is [AMOUNT], taxes are [AMOUNT] per year, insurance is [AMOUNT] per year, and utilities I cover run [AMOUNT] per month. Build me a monthly cash-flow snapshot, flag my biggest expense risks, and tell me what a healthy reserve fund looks like for a building like mine.

8. The Annual Maintenance Calendar

Create a 12-month preventive maintenance calendar for a [AGE]-year-old [BUILDING TYPE] in the Chicago climate. Organize it by month, flag the items that prevent the most expensive emergencies, and note which ones I can do myself versus which need a licensed pro.

9. Lease Renewal Letter

My tenant's lease ends [DATE]. Current rent is [AMOUNT] and I plan to renew at [AMOUNT]. Draft a friendly, professional renewal letter with the new terms, and list the notice requirements a landlord in [CITY] should confirm with the local ordinance before sending.

10. Tenant Screening Checklist

Give me a fair and legally careful tenant screening checklist for a small landlord in Illinois. Cover income verification, references, and background checks, and flag what fair housing law does not allow me to ask or consider. Remind me where to verify the current rules.

11. Improvement ROI Ranker

I have [AMOUNT] to invest in my property this year. The building is a [DESCRIPTION] in [NEIGHBORHOOD]. Rank the improvements most likely to grow my equity and my rent potential, kitchen, bath, mechanicals, curb appeal, or energy upgrades, and explain the reasoning for each ranking.

12. Energy Rebate Finder

List the energy efficiency rebates and incentive programs available to a property owner in [CITY], Illinois right now, including utility programs from ComEd and Nicor and any federal tax credits for [UPGRADE TYPE]. For each one, tell me what to search to reach the official program page so I can confirm current amounts and deadlines.
Protecting what you own

13. Squatter, the First 72 Hours

Someone is living in a unit I own at [ADDRESS]. As far as I know, I never gave this person a lease or permission to be there. Before you treat this as a squatter situation, ask me what could change that read, like a prior owner's permission, any rent I may have accepted, or an agreement I don't know about. Then walk me through a first 72 hours action plan for whichever category this turns out to be. Tell me who to call and in what order, what to photograph and document while it is fresh, and what Illinois law allows me to do and what it forbids me from doing myself. Before I act on any of it, tell me exactly what to confirm with a lawyer or the local ordinance first.

14. Notice Letter to an Unauthorized Occupant

Draft a clear, professional notice to an unauthorized occupant at [ADDRESS] who is staying there without a lease or my permission. Keep the tone firm and calm. Then tell me what Illinois and Chicago law require a notice like this to include, how it must be delivered, and flag anything I should confirm with an attorney before I send it.

15. Holdover Tenant, What Happens Next

My tenant at [ADDRESS] has stayed past the end of their lease, which ended [DATE]. Rent was [AMOUNT] per month and they are still paying it. Explain what a holdover tenancy means for me in plain language, lay out my options, the notice rules I need to confirm, and the steps in the right order. Before I choose a path, tell me exactly what to confirm with a lawyer or the local ordinance, since the right number of days and the right notice decide everything that follows.

16. Contractor Took the Deposit

I paid a contractor a deposit of [AMOUNT] on [DATE] for [WORK DESCRIPTION], and they have stopped answering and never did the work. Give me the recovery steps in the right order, who to contact, whether that is a licensing agency, a consumer protection office, or small claims court, and exactly what to gather and document to build my case. Before I file or sign anything, tell me what to confirm with a lawyer or the local ordinance, since the right venue and the deadlines depend on my specifics.

17. Inherited Property with Co-Owners

I inherited a [BUILDING TYPE] at [ADDRESS] along with [NUMBER] sibling co-owners. Help me think through how we make decisions together, how a buyout could work if one of us wants out, and how to keep the peace in the family through it. Tell me the questions to settle up front and what we should each understand before we commit. Before anyone agrees to a buyout or a sale, tell me what to confirm with a lawyer and an accountant, since title, taxes, and each person's share can be hard to undo.

18. The Unique Circumstance Master Prompt

Here is my situation: [DESCRIBE WHAT IS HAPPENING IN PLAIN WORDS]. Here is my goal: [WHAT I WANT TO HAPPEN]. Here are my constraints: [TIME, MONEY, PEOPLE, ANYTHING THAT IS FIXED]. Before you answer, tell me the assumptions you are making. Then give me concrete next steps in the order I should take them, and at the end flag what I should verify with a professional before I act.