Buying & Investing

The most expensive moment in short-term rentals is the one right before you buy, when optimism is doing the underwriting. These guides are the counterweight: how to analyze a property before you close, what the numbers actually look like once fees and vacancy show up, and which markets deserve your down payment in the first place. Sober beats sorry, and it books better too.

Start with the analytical spine — the STR ROI framework for evaluating a deal before you commit, the real-numbers comparison of Airbnb versus a long-term lease, and the honest guide to buying your first investment property, including the parts most sellers would rather skip. When you're choosing where, the best-markets breakdown pairs well with our market intelligence category and the free permit data hub, because a great cap rate means very little in a city that's about to cap your license.

The growth material lives here too: scaling from one property to ten without losing your mind or your margins, and the legal, tax, and practical guide to buying abroad for Airbnb. At the top of the market, the trophy-property studies — from Newport's gilded mansions to today's coastal estates — show how buyers of scarce assets think about value, and why those lessons trickle down to ordinary listings.

None of this is investment advice, and the guides say so themselves. It's the homework we'd want finished before wiring a deposit — and the same homework that makes the marketing easier once the keys are yours, because a property bought with clear eyes is a property that's easy to sell nightly.