Vacation Home Help

A No-BS Framework to Build a Profitable STR Portfolio (Part 2: Compliance-First Market Filter)


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Too many new investors make the same mistake: they buy a “dream” property in a market that looks good on paper — then find out the city, county, or HOA doesn’t allow short-term rentals. That’s how you end up with a liability instead of an asset.

In this episode, John Andrew breaks down Step 2 of his no-BS framework: the Compliance-First Market Filter. You’ll learn how to quickly spot STR-friendly markets, what permits and taxes you need to check before you buy, and why you should always walk away from “gray areas.”

What you’ll discover in this episode:

  • How to quickly vet states, cities, and HOAs for STR compliance
  • The permits, taxes, and occupancy rules you must confirm before making an offer
  • The Go/No-Go sheet that saves you from wasting capital on bad deals
  • Why walking away from gray markets protects your long-term portfolio

👉 Follow John Andrew for daily STR insights:

  • Facebook: @thejohnandrew
  • Instagram: @thejohnandrew

💡 Need help running your STR hands-free? With John Andrew’s flat-fee co-hosting service, you keep control of your listing and payouts — while his team handles guest communication, pricing, cleaners, and compliance. No commissions, no surprises. 👉 book a call at calendly.com/johncandelario/cohosting-discovery-call.

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