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 

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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 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

On this week’s episode of Short Term Rental Management, Luke digs into why you should always assume user error first when guests report that something is “broken,” using real-world examples like HVAC issues and TV/Roku remotes to show how basic property knowledge and calm troubleshooting can save you time, money, and stress. He also talks about why a quick phone call can turn a frustrated guest into a satisfied one, and how presenting yourself as a professional operation (even with just one property) helps you handle problems more smoothly.

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 dives into “The Word Yes” and how a simple mindset shift can dramatically improve your guest experience and reviews. Reflecting on the post-COVID era, Luke explains why hosts can no longer afford to say no to small requests like paper towels or detergent, and how embracing flexibility pays off in long-term success.

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 why he believes “repeat guests are for suckers” and why obsessing over getting people back to the same property is usually a poor use of time. He contrasts the heavy effort of building repeat-guest lists, direct booking systems, and loyalty-style incentives with simply leveraging platforms like Airbnb and Vrbo, which already spend massive amounts on marketing to bring in an endless stream of new guests. Along the way, Luke shares personal stories about travel habits, Disney trips, gas-price frugality, and mindset, all to drive home the point that your house isn’t that special, you’re a landlord first, and your energy is better spent finding new guests than clinging to the same ones.

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