If someone handed you $250,000 in cash to invest in a short-term rental, where would you buy and what strategy would you use to make that money work?

In this episode of the Cash Flow Positive Podcast, host Kenny Bedwell is joined by Erin Wegrzyn, a real estate consultant with STR Insights, to explore exactly that scenario. Together, they break down how to choose the right markets, set realistic expectations, and avoid the “amenities arms race” that eats into cash flow.

Erin shares her journey from long-term rental investor to short-term rental specialist and why her strategy has shifted toward properties that both cash flow and create memories for her family. Kenny and Erin discuss how to research markets, stay ahead of competitors, and build a property that can grow with the market over time, without burning out or over-renovating.

If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

• How to choose markets without spreading yourself too thin
• Why being “one of one” in a market is a huge advantage
• How to avoid competing in an endless amenities war
• What to look for in properties that allow for future upgrades
• Why following where large investors are putting money can reveal emerging markets
• The best way to build a reliable local team of contractors and cleaners
• Why you should visit and experience a market before you invest there
• And much more...

Guest Bio:

Erin Wegrzyn is a real estate consultant with STR Insights, where she helps investors analyze markets and identify profitable short-term rental opportunities. Based in Kentucky, she brings firsthand experience as an investor and a deep understanding of market trends, property selection, and building reliable local teams. Erin is passionate about helping clients choose properties that cash flow, grow in value, and fit their lifestyle goals.

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

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.

• STR Insights software
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• Top Markets Report (via STR Insights website)
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• Dave Ramsey podcast (benchmark reference)
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• Zillow & Redfin (for market comps)
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• 🌐 STR Insights
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• 🎧 Cash Flow Positive Podcast
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• 📲 Instagram – @kenny_bedwell
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• ▶️ YouTube – Cash Flow Positive
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• 💼 LinkedIn – Kenneth Bedwell

What does Airbnb’s latest fee increase mean for your bottom line, and how should it change the way you evaluate deals?

In this episode of the Cash Flow Positive Podcast, Kenny Bedwell sits down with Rachel Gniady, full-time real estate investor and STR Insights consultant, to talk about how the new 15.5% host fee is reshaping underwriting, deal selection, and long-term strategy.

Rachel shares how she is being even more conservative with revenue estimates, why she is rejecting deals that don’t have a wide enough margin, and why being “one of one” in a market is more important than ever. Together, Kenny and Rachel dive into moats, market trends, appraisals, and the importance of thinking like an investor first, even as competition heats up and the “middle” of the STR market gets squeezed.

Want to keep spotting high-margin STR deals even as fees climb? Listen now and sharpen your strategy. If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!

Key takeaways:

• Why Airbnb’s fee change demands more conservative underwriting
• How to evaluate properties with a “good, better, best” revenue approach
• Why being unique in your market protects your profits
• The dangers of chasing trends and how to know when to walk away
• Why comps, cost basis, and appraisals matter more than ever
• How to protect yourself in today’s “Wild West” real estate market
• Why stability can beat higher short-term returns in the long run
• The importance of making offers quickly and confidently
• And much more...

Guest Bio:

Rachel Gniady is a full-time real estate investor and consultant for STR Insights, where she has helped over 50 clients close deals and build profitable short-term rental portfolios. Based in New Orleans, she has nearly 20 years of experience buying, improving, and selling properties.

Resources:

Connect with Kenny on LinkedIn

Follow Kenny on Instagram

Part 2: Finding High ROI STR Deals with No Money with Rachel Gniady

Connect with Rachel on LinkedIn

Disclaimer:

The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.