Cash Flow Positive 2026 Predictions and 2025 Market Recap
Are you one tough market away from making or breaking your STR dreams? In this eye-opening solo episode, Kenny Bedwell delivers his no-BS, data-driven breakdown of 2025’s market shakeups and lays out urgent, can’t-miss predictions for 2026.
With competition at a boiling point and Airbnb’s pricing bombshell still sending shockwaves, Kenny Bedwell exposes where investors keep getting crushed, and who’s quietly winning big. From wild price slashes to the “big fish or die” investor mentality, this episode is packed with the kind of ruthless honesty and hard metrics you won’t get from any hype-driven guru.
Tune in now or risk fumbling the next 12 months. Discover the exclusive moves smart investors will make next, before the rest of the market catches on, and before average operators are left behind for good.
Timestamped Highlights
[00:00] – Why “average” properties are getting destroyed while 90th percentile performers quietly flourish
[00:03:51] – The mindset shift every STR buyer must make now to avoid draining cash flow
[00:06:26] – Markets you’d written off are making a shocking comeback—here’s why
[00:08:17] – Explosive legal shakeups: Are STRs still real estate or something else?
[00:10:33] – The Airbnb fee switch: How hosts are sabotaging themselves and tanking in search rankings
[00:13:10] – The real reason your smart price hikes backfired—and how to break the algorithm instead
[00:18:46] – The “turnkey trap”: Why offloading STRs is about to flood the market (and what smart buyers must do now)
[00:24:33] – Surprise winners & fallen stars: The brutally honest 2026 top markets preview
[00:26:31] – Kenny’s wild 2026 prediction: The coming Airbnb “pay to play” era
Mentioned Resources
- STR Scale Summit (event)
- Top Markets Report (via STR Insights)
- Airbnb Luxe
- Airdna (STR market data)
Important Links
- Want us to find the deals for you? https://strinsights.com
- Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df
- Instagram – @kenny_bedwell
- YouTube – Cash Flow Positive
- LinkedIn – Kenneth Bedwell
Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.