How To Underwrite A Short Term Rental

Fail forward, buy smarter. In this solo deep-dive, Taylor breaks down real-world STR underwriting—no hype, just numbers. If you’ve ever “made a spreadsheet sing” to justify a deal, this one’s for you. Learn the exact framework he’s used to evaluate hundreds of thousands of properties over the past four years and how to stay disciplined when emotion wants the win.What you’ll learnThe anatomy of a winning pro forma: purchase price, debt structure, closing costs, and true Total OOP (down payment, reno, amenities, furniture, vendors).Building an optimization list that actually moves RevPAR (from paint to pickleball).Revenue the right way: comping like-for-like, using data tools (AirDNA/Rabbu), and modeling Low / Mid / High scenarios.Expense reality check: utilities, supplies, PM software, cleaning fees in vs. invoices out, HOA, taxes, insurance, CapEx & reserves.NOI vs. Free Cash Flow: what lives “above the fold,” why debt service ≠ mortgage, and how to compare deals apples-to-apples.Return stack 101: cash-on-cash, principal paydown, long-view appreciation (why you should zoom out 20–25 years), and a primer on the STR tax play.The baseball mindset: why looking at hundreds of deals to land a few great ones is normal—and healthy.__Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 265+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com