On this week's episode of Short Term Rental Management, Luke explains why smaller, more affordable short-term rental homes are often easier to keep booked than large, high-dollar properties. He walks through the psychology of guest demand, noting that two and three bedroom homes tend to book faster because they fit more travelers’ budgets and search behavior, even when priced similarly to larger homes. Luke also ties this back to a long-term rental mindset, emphasizing that at the end of the day, it’s “just a house,” and steady, consistent demand often beats chasing premium amenities or oversized properties.

How to connect with Luke:

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

Short Term Shop Plus - stsplus.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 Airbnb’s new “date-specific cancellation policies” rollout, which lets hosts set different cancellation rules for different dates on the calendar (with the policy determined by the guest’s check in date). He walks through how the feature works and why it matters. Luke also briefly reviews Airbnb’s current cancellation policy options and notes this is Airbnb-only for now, with hopes it eventually becomes manageable through PMS tools via the API.

How to connect with Luke:

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

Short Term Shop Plus - stsplus.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 shares a candid and unfiltered story about getting fired by a long-term property management company—and the hard lessons that came with it. He walks through red flags like inexperienced managers, poor inspections, inflated rehab estimates, and conflicts of interest, while owning his own mistakes around communication under pressure. The episode serves as a real-world reminder of why vetting managers, setting expectations, and staying involved in asset oversight matter just as much as choosing the right market.

How to connect with Luke:

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

Short Term Shop Plus - stsplus.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 is joined by Libby of Co Host Oklahoma to unpack what it really takes to scale a co-hosting and property management business to 45+ units. They dive into balancing owner expectations with guest experience, navigating a high-profile $16,000 damage claim, and building scalable systems using tools like Hospitable, PriceLabs and custom automation. The conversation also explores branding, networking, co-hosting vs. property management, and why quality, simplicity, and strong relationships matter more than over-the-top amenities.

How to connect with Libby:

• Website: https://cohostoklahoma.com

• Direct booking: https://hostlahoma.com

• Instagram & Facebook: @CoHostOklahoma

How to connect with Luke:

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

Short Term Shop Plus - stsplus.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 sits down with David to unpack his journey from a full-time engineering career to owning six short-term rentals and managing more than 35 units for other investors. David shares how he leveraged disciplined investing, systems, and team building to scale, why pricing and operations matter more than hype, and what it really takes to leave a W-2 job for long-term freedom through real estate. The conversation dives deep into property management realities, software stacks, staffing, and why adaptability and honest pricing are essential in today’s STR market.

How to connect with David:

• Website: https://shorttermconnections.com

• Direct booking brand: https://865vacations.com

• Instagram & TikTok: @865Vacations

How to connect with Luke:

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

Short Term Shop Plus - stsplus.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 explains how short-term rental success often depends on balancing two different mindsets: the creative right brain and the analytical left brain. He breaks down how creative operators excel at design, guest experience, and listings but often struggle with pricing and numbers, while analytical operators thrive on spreadsheets and projections but may overlook presentation and communication. Luke’s key takeaway is that understanding your natural strengths—and intentionally shoring up your weaknesses—is critical to running a profitable, sustainable STR business.

How to connect with Luke:

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

Short Term Shop Plus - stsplus.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 breaks down two recent SOP failures—when a deadbolt and backup lockbox both failed—and explains why that kind of catastrophic access breakdown is preventable with better systems. He shares practical fixes like replacing unreliable push-button lockboxes, tracking deadbolt install dates and lockbox details in a spreadsheet, and implementing a semiannual lockbox function test so you’re never scrambling during guest check-in.

How to connect with Luke:

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

Short Term Shop Plus - stsplus.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 sits down with bookkeeper and real estate investor Ben Day of Lionshare Bookkeeping to demystify bookkeeping for short-term rental owners, from when you actually need a bookkeeper versus just a CPA to what clean books should look like. They dig into pricing for bookkeeping services, the difference between simple landlord books and complex trust accounting for property managers, and the tech stack Ben recommends—including tools like Tally Breeze, Get Clearing, Relay Financial, and QuickBooks Online to streamline STR finances and owner statements.

How to connect with Ben:

https://lionsharebookkeeping.com/

How to connect with Luke:

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

Short Term Shop Plus - stsplus.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