If $250,000 dropped into your lap today, would you actually know what to do with it?

In this episode of Cash Flow Positive, Kenny Bedwell pulls back the curtain on exactly how he’d put that money to work in short-term rentals. He breaks down why your financing strategy can make or break a deal, the five cost buckets most investors forget about, and why setting your ROI goal up front is non-negotiable.

You’ll hear Kenny think through real markets, from Florida beaches to Shenandoah cabins, and explain how to spot which ones fit your budget and which ones will bleed you dry.

Don’t guess your way into a $250K mistake. Hit play now to hear Kenny’s no-fluff, data-backed roadmap and get clarity on where your money will actually cash flow.

Timestamped Highlights

[00:00] How a $250K windfall changes your investing strategy overnight

[02:14] The financing trap that torpedoes deals before they close

[04:18] The five hidden costs every STR investor must budget for

[07:36] Kenny’s minimum ROI goals—and why cash flow beats percentages

[10:53] The “process of elimination” method for picking your markets

[14:25] Why Bradenton, FL, might work—and the brutal barrier to entry

[21:00] Shenandoah’s low-barrier charm vs. beach market competition

[24:38] How lakefronts in Michigan and urban rentals in Cincinnati stack up

Resources

STR Insights software
Top Markets Report (via STR Insights website)
Dave Ramsey podcast (benchmark reference)
Zillow & Redfin (for market comps)

Evergreen Links

Want us to find the deals for you? https://strinsights.com
Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
📲 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 and Podcast Your Brand. Production and editing by Podcast Your Brand.

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