How to actually find and secure profitable properties

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.

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

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.