How Do You Know When It’s Time to Sell? The Real Math Behind a 1031 Exchange | Kenny Bedwell

Описание: What if leveling up your real estate portfolio was easier than you think?

And what if one smart move could help you avoid capital gains, grow long-term wealth, and invest with confidence?

In this episode of Cash Flow Positive, Kenny Bedwell breaks down the 1031 exchange process in the simplest way possible. If you're thinking about real estate investing, short-term rentals, or upgrading your rental property investing strategy, this guide helps you avoid the biggest mistakes and understand the timelines clearly.

We talk about the 1031 exchange basics, the 1031 exchange timeline, what the IRS actually requires, and how to prepare before you sell your property. Kenny also explains return on equity, why some owners hold “sleeping equity,” and how to decide if it’s time to sell.

You’ll also learn the pros, cons, and hidden traps of doing a reverse 1031 exchange, using a qualified intermediary, and how to plan your next move without stress. Whether you want to scale into commercial real estate deals, buy another STR, or protect future cash flow, this episode gives you the clarity you need.

If you’re part of the Cash Flow Positive community, thinking about the STR real estate world, or planning your next big step in long term investing, this breakdown will help you level up your strategy with simple, practical steps.

TIMESTAMPS:
[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:
STR Scale Summit (event): https://strscalesummit.com
STR Insights software: https://www.strinsights.com/software
IRS Section 1031 (1031 exchange rules): https://www.irs.gov/pub/irs-news/fs-0...
QI / 1031 Intermediary services: https://www.irs.gov/businesses/corpor...
Return on Equity (ROE) audit: https://bit.ly/3NfRRJe

Important Links
Connect with Kenny on LinkedIn:   / kenneth-bedwell-9680a8113  
Follow Kenny on Instagram:   / kenny_bedwell  
Want us to find the deals for you? https://strinsights.com
Get Top Markers for STRs (2025) https://www.strinsights.com/top-inves...

🎯 Subscribe for more insider tips on real estate, investing, and building a profitable vacation rental business:   / @cashflowpositivepodcast  

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