Are you scared of losing tens of thousands to the IRS on your next property sale? Wondering if a 1031 exchange is really the secret weapon for building unstoppable cash flow… or just a headache waiting to happen?

This episode, Kenny Bedwell, no-fluff educator and the data-driven mind behind STR Insights, breaks down exactly how to prepare for a 1031 exchange the right way—using numbers, timelines, and real investor mistakes. From crushing the fear of tax bills to unlocking hidden strategies for short-term rental success, Kenny’s frank approach is full of hard truths and simple steps.

Listen now to sidestep costly errors, dodge timeline traps, and discover insider tactics you won’t hear anywhere else. Miss this episode, and you risk making one of the most expensive mistakes in real estate. Tune in while the stakes are high and every dollar counts!

[00:00] The hidden 1031 pitfalls that even experienced investors miss

[00:01:14] Why “waiting until closing” could wreck your 1031 dreams

[00:02:12] The shocking impact of capital gains—the numbers that matter now

[00:03:16] How to use the IRS rules to your advantage (and avoid a nightmare)

[00:05:13] The #1 reason most investors lose money on STR furnishings

[00:07:37] The uncommon truth about 1031 down payments and boot traps

[00:11:03] Kenny’s proven equity audit method: Should you sell or wait?

[00:14:04] Mapping your cash flow and equity for a powerful portfolio move

[00:16:50] When you should start hunting for your next market (spoiler: it’s not what you think)

[00:20:46] The 60-day strategy no one is teaching for stress-free 1031 shopping

[00:22:03] The risky world of reverse 1031 exchanges—what you must know

1. STR Scale Summit (event)
2. STR Insights software
3. IRS Section 1031 (1031 exchange rules)
4. QI / 1031 Intermediary services
5. Return on Equity (ROE) audit

1. Want us to find the deals for you? https://strinsights.com
2. Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df
3. Instagram – @kenny_bedwell
4. YouTube – Cash Flow...

Are you terrified of sinking your cash into a dying market or worse, following the herd off a financial cliff? In this masterclass episode, Kenny Bedwell rips the lid off his 2026 Top STR Markets Report, arming you with the real numbers, raw pitfalls, and hidden opportunities no one else will dare mention.

You’ll hear the unbiased, hard-hitting truth: where data says to buy, where strict regulations ruin even the prettiest towns, and razor-sharp strategies to squeeze maximum ROI in a landscape rocked by new rules and unpredictability. Kenny reveals not only the top 10 investable markets, but exactly why they’re worth your attention (and why some previous darlings are falling off).

Do not wait. Miss this, and you’re risking real money, real time, and watching your freedom slip away, while others secure the deals that change their financial destiny. This episode gives you numbers, biases called out, and actionable steps you won’t get anywhere else.

[00:01] – Why most “top STR market” lists are wrong (and what everyone’s missing)

[00:10] – The wild, thrilling impact of new regulations and market shakeups—this year’s biggest surprises revealed

[00:23] – Kenny’s ultra-candid red light, green light analysis: Where you really should be scared (and where to pounce)

[00:46] – The shocking climb of Mohican State Park and the overlooked cash cows in rural regions

[01:13] – Dirty little secrets behind high-grossing mountain and lake towns (and why access and permits matter more than hype)

[01:38] – Are you sitting on cash? Kenny reveals the uncommon ways budget transforms your deal-finding lens (with 4 ROI-driven categories)

[01:57] – How to beat city restrictions with region plays and advanced location hunting—no more bureaucratic land mines

[02:15] – The final, blunt warning: What happens if you listen to influencers over the data... and why you can’t skip this download

1. STR Scale Summit (event)
2. Airdna (STR market data)
3. BiggerPockets
4. Interview reference: "Part 2: How to make over $500k on one STR with Jeff Usner” episode, August/September 2024

1. Want us to find the deals for you? https://strinsights.com
2. Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df
3. Instagram – @kenny_bedwell
4. YouTube – Cash Flow Positive

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.

[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

1. STR Scale Summit (event)
2. Top Markets Report (via STR Insights)
3. Airbnb Luxe
4. Airdna (STR market data)

1. Want us to find the deals for you? https://strinsights.com
2. Get Top Markers for STRs (2025) - https://rebrand.ly/28b1df
3. Instagram – @kenny_bedwell
4. YouTube – Cash Flow Positive
5. 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.