Short Term Rental Management

On this week’s episode of Short Term Rental Management, Luke chats with Jeremy Udovich of Sheboygan Vacation Rentals, who’s building a thriving short-term rental business in Wisconsin while still working full-time in tech. Jeremy shares how he and his sister grew from one property to a co-hosting portfolio of 19 units—without burning out. They discuss automation, working with family, market seasonality, and the importance of hospitality (including the golden rule: “give them the pickle”). Jeremy’s measured, sustainable approach to growth highlights how keeping your day job can actually accelerate real estate success. 

How to connect with Jeremy: sheboyganvacationrentals.com

How to connect with Luke:

The Short Term Shop - https://theshorttermshop.com/

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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 of Short Term Rental Management, Luke is joined by Rubin Horowitz, founder of STR Super Cleaners, a rapidly growing short-term rental cleaning company operating in multiple U.S. markets. Rubin shares how he scaled from solving his own cleaning headaches in the Poconos to managing over 700 properties across markets like the Smokies, Emerald Coast, and Nashville. They dive deep into automation, team building, property maintenance support, and how his company partners with hosts and managers while steering clear of full property management. Reuben also offers tips for creating five-star guest impressions—like integrating welcome screens and maintaining scent standards.

Visit strsupercleaners.com to request a quote or consultation

How to connect with Luke:

The Short Term Shop - https://theshorttermshop.com/

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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 of Short Term Rental Management, Luke is joined by Short Term Shop Plus coach Chuck Kramer to discuss whether it's appropriate for Airbnb cleaners to request tips. Both Luke and Chuck come out in favor of allowing tipping—drawing from their personal experiences in hospitality—but agree that leaving tip envelopes labeled “The Management” crosses a line into tacky. They emphasize that subtle, respectful options (like countertop signs or guidebook mentions) are a better alternative for encouraging gratuity without pressuring guests.

How to connect with Luke:

The Short Term Shop - https://theshorttermshop.com/

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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 of Short Term Rental Management, Luke reflects from New Orleans on the changing tides in real estate investing and pays tribute to personal heroes Ozzy Osbourne and Hulk Hogan. He shares updates on a new beach house rehab project and emphasizes that while real estate is currently “not cool,” that perception presents an opportunity for disciplined investors. Luke argues that public sentiment, not interest rates, is the real market barrier—and encourages listeners to stay persistent, find motivated sellers, and act before the market becomes “hot” again.

How to connect with Luke:

The Short Term Shop - https://theshorttermshop.com/

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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 of Short Term Rental Management, Luke is joined by guests Jeff and Jenny, first-time short-term rental investors who share their journey of overcoming a major challenge: their well running dry just months after purchasing a Smoky Mountain cabin. The couple recounts navigating the emotional and financial stress, installing a 1,000-gallon water storage system, and maintaining a positive mindset through it all. They also discuss what they’ve learned about resilience, systems, and generational wealth. 

How to connect with Luke:

The Short Term Shop - https://theshorttermshop.com/

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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 of Short Term Rental Management, Luke Carl shares a personal milestone—he’s selling one of his vacation rental homes. He opens with a humorous tale about replacing a toilet valve himself, then dives into the reasoning behind the sale, including shifting family preferences, property management logistics, and market timing. Luke reflects on pricing strategy, buyer behavior, and current real estate trends, emphasizing that sellers need to be realistic in 2025's slower market.

How to connect with Luke:

The Short Term Shop - https://theshorttermshop.com/

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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 of Short Term Rental Management, Luke sits down with Miles from Hospitable for an in-depth discussion on the evolution and current state of property management software. They cover Hospitable’s recent dynamic pricing launch, AI-powered tools like the Knowledge Hub and Copilot, and how sentiment analysis is flagging guest issues in real time. The conversation also touches on the growing momentum behind direct bookings and the future of PMS as a “short-term rental super app.” 

How to connect with Luke:

The Short Term Shop - https://theshorttermshop.com/

Follow us on Instagram 

Follow us 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 of Short Term Rental Management, Luke takes listeners through a string of recent challenges he faced in the world of property ownership—from termites and fire damage to a $46,000 miscommunication with a vendor. He walks through seven issues in total, including an inherited tenant move-out requiring a full unit renovation, a fragrance-sensitive guest, and a collapsing porch post that turned out to be decorative. Through it all, Luke emphasizes the importance of communication and staying resilient as a property owner.

How to connect with Luke:

The Short Term Shop - https://theshorttermshop.com/

Follow us on Instagram 

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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 of Short Term Rental Management, Luke breaks down the eight biggest mistakes he sees short-term rental owners make. From rushing into deals without patience, to poor guest communication, neglecting pricing and finances, and underestimating the true cost of real estate, Luke delivers a rapid-fire reality check.

How to connect with Luke:

The Short Term Shop - https://theshorttermshop.com/

Follow us on Instagram 

Follow us 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 of Short Term Rental Management, Luke interviews Ryan Ferguson, an electrician-turned-hot tub repair expert serving East Tennessee's Smoky Mountains. They dive into common hot tub issues in vacation rentals—like economy mode, airlocks, and water damage from improper draining—while sharing maintenance tips, regulatory insights, and hilarious stories involving bears, raccoons, and overloaded tubs. Ryan also emphasizes the importance of simplicity, proper electrical installation, and regular inspection to keep STR hot tubs guest-ready and code-compliant.

How to connect with Ryan:

Website

Phone #: (865) 635-9383

Email: [email protected]

How to connect with Luke:

The Short Term Shop - https://theshorttermshop.com/

Follow us on Instagram 

Follow us 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