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!

Timestamped Highlights

[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

Mentioned Resources

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.

Part 1: Preparing For A 1031 Exchange The Right Way