Part 2: If you had $250k to invest, where should you go?

Sep 25, 2025

In this discussion, Erin Wegrzyn, a real estate consultant specializing in short-term rental strategies, shares her journey from long-term rentals to her focus on family-friendly STRs. She delves into the importance of choosing the right markets and how to avoid the tempting but costly amenities arms race. Erin emphasizes researching emerging markets, building a reliable local team, and the value of hands-on experience before investing. Plus, she offers key insights on setting realistic ROI goals and leveraging community resources for untapped rental destinations.

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ADVICE

Buy For Bedroom Count And Upgrade Path

Evaluate what your purchase budget actually buys: bedroom count, amenity needs, and scalability.
Prefer markets where you can start with basics and add amenities over time rather than needing all amenities day one.

INSIGHT

Find Emerging Markets By Listening Locally

New vacation markets often surface from friends' travel patterns rather than top-10 lists.
A single person naming a place can trigger deeper research and reveal underserved drivable destinations.

ADVICE

Follow Big Investors To Spot Growth

Track where big money and major developers buy land to spot emerging growth areas.
Follow large investors' moves to anticipate new attractions and demand before markets saturate.

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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

Cash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights. Production and editing by Podcast Your Brand.

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.