REPS Analyzer

Stress-test the "buy a short-term rental, pay less tax" idea before you bet real money on it.

the need

There's a pitch that eventually finds every high-earning household: buy a short-term rental, qualify as a real estate professional, and let the paper losses from depreciation shrink your tax bill. The numbers in the pitch always work — partly because the people running them usually make money when you say yes.

My friends and I needed a way to run the whole deal ourselves, with nobody selling anything: every dollar in and out, in the order it actually happens, before talking to anyone with a stake in the answer.

what it is

A calculator that lays the full strategy out for your actual numbers. It shows what you'd need in the bank before closing — down payment, closing costs, and a real cash reserve measured in months of runway — then the ongoing picture of rent coming in versus everything going out: mortgage, insurance, property tax, empty nights, repairs, platform fees. Then it shows what the Year 1 bonus-depreciation tax savings would actually mean for your household, and how that big first year compares to the years after it.

The defaults are deliberately skeptical. Occupancy estimates get a buffer, because the listing-site numbers skew optimistic. And every output says what it is right on the label: a planning estimate to take to your CPA — not a buy decision.

who it's for

Households who keep hearing this strategy — from a coworker, a podcast, a very confident guy at a barbecue — and want to pressure-test it with their own numbers before it costs them real money.

what I learned building it

• The tax savings are real, and so is everything around them. The Year 1 number in the pitch is genuine. What the pitch skips is the cash you need before closing, the months of reserves, and the nights the place sits empty. The deal only makes sense — or doesn't — when all of it is on one screen.
• Defaults are a point of view. Every optimistic default quietly nudges someone toward buying. I made mine lean the other way on purpose, and being forced to pick a stance for every single field taught me more about the strategy than any article had.
• Order matters as much as amounts. The cash goes out at closing; the tax refund arrives much later. Showing every dollar in the sequence it happens changes how the same deal feels.
• Saying what the tool isn't builds more trust than what it is. "Estimates only — verify with your CPA" appears throughout, and that honesty is what makes people comfortable putting real numbers in.

where it is now

It's ready to use — free, nothing to sign up for. It won't tell you to buy or not to buy. It puts the whole picture in front of you, so that when you do sit down with your CPA, the conversation starts from real numbers instead of the pitch.

Got pitched this strategy? Run your numbers, then tell me what surprised you →