Avery is joined by Jeremy Udovich, founder of Sheboygan Vacation Rentals, to discuss how he went from a career in golf and software sales to building a thriving short-term rental portfolio and management company in Wisconsin. Jeremy shares how a single property near Lake Michigan grew into a portfolio of owned and managed vacation rentals, why Sheboygan’s beaches, golf courses, racetrack, and outdoor recreation create strong year-round demand, and how access to capital helped him scale quickly. He also explains why he waited years before leaving his W-2 job, the importance of education and preparation before taking on risk, and what he looks for when deciding whether to manage a property for another owner. The conversation offers valuable insight into scaling responsibly, building a management business organically, and finding overlooked opportunities outside of traditional vacation rental hotspots.

Connect with Jeremy:

www.sheboyganvacationrentals.com

Connect with us:

The Short Term Shop - https://theshorttermshop.com/
https://stsplus.com/
Follow Avery Carl on Instagram
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Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week's episode, Avery is joined by Kelsey Ardoin to break down what’s working right now in the Galveston and Crystal Beach short-term rental market. Using one of her own properties as a case study, Kelsey shares how investors can dramatically improve bookings without spending tens of thousands on major renovations, focusing instead on guest experience, outdoor entertainment spaces, hot tubs, and highly photographable amenities. She explains why large-group properties continue to perform well in this drive-to market, how to design beach houses that stand out from the competition, and why maximizing comfortable sleeping arrangements is critical to success. Avery and Kelsey also discuss current market conditions, why Crystal Beach remains one of the more affordable beach investment markets in the country, and how today’s buyer-friendly environment compares to the frenzy of the COVID-era boom.

Connect with Kelsey:

agents@theshorttermshop.com

Connect with us:

The Short Term Shop - https://theshorttermshop.com/
https://stsplus.com/
Follow Avery Carl on Instagram
Follow Avery Carl on TikTok
Join the Short Term Shop Facebook group
Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week's episode, Avery is joined by Chris McKenna, a former Fortune 500 executive who retired at 49 after building a portfolio of short-term rentals across Alabama, Oklahoma, and Maine. Chris shares how hearing Avery on a BiggerPockets podcast sparked his real estate journey, leading him from a demanding corporate career to owning multiple vacation rental properties that now generate nearly $1 million in annual revenue. He recounts the unforgettable challenges of his first investment property—including a renovation disaster that landed him in the emergency room with Bell’s palsy—and explains why staying focused on long-term goals helped him keep moving forward. Chris also discusses scaling a portfolio across multiple markets, transforming underperforming properties through strategic upgrades, and the lessons he learned from purchasing and revitalizing a lakeside cabin resort in rural Maine.

How to connect with Chris:

https://lawrenceslakesidecabins.com/
https://vandellvacationrentals.com/gulfshores/

Connect with us:

The Short Term Shop - https://theshorttermshop.com/
https://stsplus.com/
Follow Avery Carl on Instagram
Follow Avery Carl on TikTok
Join the Short Term Shop Facebook group
Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon