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.

Ask episode

AI Snips

Chapters

Transcript

Episode notes

ANECDOTE

Journey From Long-Term To STR Specialist

Erin described starting in 2016 with long-term rentals before discovering a passion for short-term rentals and hospitality.
She transitioned from investor to realtor to consultant focused solely on STRs in Kentucky.

ANECDOTE

Buying For Family Use And Cashflow

Erin bought a family-friendly STR near Branson so her kids could enjoy it and she could actually relax there.
She values properties that serve both as investments and family memories rather than pure cashflow assets.

ADVICE

Buy Truly Turnkey, Not Major Reno Projects

Prioritize turnkey properties to avoid long contractor projects and constant on-site renovations.
Accept small fixes like paint or a vanity, but avoid homes needing full kitchen or structural remakes.

Get the Snipd Podcast app to discover more snips from this episode

Get the app

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.