Listing-side work

The "should we sell" conversation

A homeowner asks what their place is worth and whether to sell, rent it out, or stay. Hand them a scenario memo instead of a guess, and be the agent they call when they decide.

The idea

What this does

Years before a listing, homeowners circle the question: what would we walk away with, should we rent it instead, does the move even pencil. This prompt builds the honest answer for one household: a value band from real nearby sales, the net-proceeds math with every deduction visible, the rent-versus-sell comparison, and the tax-shaped flags (the two-of-five-year rule, California's Prop 19 portability for 55-plus moves) framed as questions for their CPA. It is a service you can give a past client in fifteen minutes, and it plants the listing conversation in evidence.

Gather these first

Before you start

The home's address and rough details, plus what they paid and when if you know it
Their mortgage ballpark: balance and rate (they usually know)
What they are weighing: sell to upsize, rent it out and move, or stay put
Web search turned on in your AI tool

Step by step

How to use it

Start a new chat named for the household.
Copy the prompt, fill in what you know, and paste; it will ask for the gaps.
Check the value band against your own comp sense; you are the market expert, and your adjustment sharpens the memo.
Deliver it personally, not as a blast; this is a relationship touch wearing a spreadsheet.

Copy everything in the box

The prompt

Paste this into your AI tool Fill anything in [BRACKETS] with your details

You are a housing-decision analyst helping me, a residential real-estate agent, prepare a "sell, rent it out, or stay" memo for homeowners I know. Use live web search for comparable data; source what you find. Where personal tax or lending details matter, frame them as labeled questions for their CPA or lender, never as advice. The household: own [ADDRESS/DESCRIPTION], bought [YEAR, ~PRICE if known], mortgage roughly [$BALANCE at RATE%], considering [e.g. selling to move closer to grandkids / renting it out and relocating / staying and remodeling]. Timeline feeling: [e.g. within a year / someday / just curious]. Step 1: ask me in one batch for anything essential I have not given you, then proceed with labeled assumptions. Step 2: produce the memo. 1. VALUE BAND. What nearby comparable sales suggest today, as an honest RANGE with the comps listed and linked. State clearly this is a starting band, not an appraisal or a promise. 2. NET IF SOLD. Walk the math visibly: band midpoint and edges, minus commission [X]%, typical closing costs for [COUNTY], mortgage payoff, and moving reality. Show the walk-away range. 3. RENT-IT-OUT SCENARIO. Realistic rent from current local listings (linked), minus the honest costs (vacancy, maintenance, management, insurance change), against their payment. One paragraph on what being a landlord of this specific home would actually be like. 4. THE TAX-SHAPED FLAGS. In plain English, the questions worth asking a CPA before deciding, likely including: the primary-residence capital-gains exclusion and its two-of-five-year clock (especially if they rent it out first), property-tax basis implications of moving (in California, Prop 19 portability for 55+), and anything their numbers suggest. Questions, not conclusions. 5. SIDE BY SIDE. The three paths (sell now, rent out, stay) compared on: cash effect, monthly effect, flexibility, and risk, each in one honest line. 6. WHAT WOULD MAKE THIS EASY. The two or three facts (a real appraisal, a lender letter, a CPA answer) that would turn this from scenarios into a decision, and who provides each. Rules: ranges and sources for every market claim, assumptions labeled, warm plain tone, zero pressure toward selling; the memo serves their decision, whichever way it goes.

→Anything in [BRACKETS] is yours to fill in. Delete a bracket line if it does not apply; the prompt still works.

The result

What you'll get back

A sourced value band and a visible walk to the net number
The rent-versus-sell comparison grounded in current local rents
Tax flags translated into CPA questions the household will actually ask
A three-path summary that respects "stay" as a real answer
The follow-up list that naturally includes you

Level it up

Make it yours

Run it before the coffee, not after; arriving with the memo is the move.
Ask for "the two-paragraph version for a text message" when the relationship is casual.
Revisit annually: same chat, "update this with current data," and the touch becomes a ritual (the heart of playbook 21).

Keep it honest

The zero-pressure rule is the whole play: a memo that respects "stay" earns the listing when the answer becomes "sell."
Value bands from web comps are a starting point; your CMA (playbook 05) replaces them the moment things get real.
Tax questions go to the CPA every time; the memo names the questions precisely so the CPA visit is short.