💡 What if there’s a way to slash your tax bill while building real estate wealth—without buying a single new property?

In this episode, we turn the spotlight on one of the most powerful, yet often overlooked, wealth-building tools for investors: tax strategy. Eric Oliver of Maven Cost Segregation to break down, in plain English, how cost segregation and 100% bonus depreciation can dramatically reduce your taxes—especially if you own or plan to own short-term rentals.

Eric explains how accelerated depreciation really works, what the so-called “short-term rental loophole” is (and isn’t), and why material participation and intent are key in the eyes of the IRS. Jason and Rory go even further, sharing real numbers from their own portfolio, including how they used a look-back study and a “poor man’s reverse 1031” strategy to offset a large tax bill after selling a property.

If you’ve ever thought taxes were just an unavoidable cost of investing, this episode will make you see them as a strategic wealth-building tool.

Things we discussed in this episode:

1. Cost segregation basics – accelerating depreciation by breaking a property into components with shorter lives.
2. Bonus depreciation – how 100% bonus magnifies cost seg savings in year one.
3. STRs vs. LTRs – why short‑term rentals can offset W2 income but long‑term rentals usually can’t.
4. “Short‑term rental loophole” – a legal, code-based strategy, not a shady trick.
5. Material participation – key IRS tests, especially 100 hours and more time than anyone else.
6. Timing a purchase – buying late in the year to more easily document material participation.
7. Jason & Rory’s $900k deal – large depreciation created, especially from exterior work and landscaping.
8. “Poor man’s reverse 1031” – using cost seg to help offset capital gains from a property sale.
9. Look‑back studies & Form 3115 – reclaiming missed depreciation from prior years.
10. Tax planning strategy – using cost seg selectively to manage tax brackets and avoid wasting deductions.

Get in touch with ERIK:

Facebook - ⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/people/Maven-Cost-Segregation-Tax-Advisors/61570153671981/

Instagram - https://www.instagram.com/mavencostseg/

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://mavencostseg.com/erik/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #VacationRentals #CostSegregation #BonusDepreciation #TaxStrategy#RealEstateTax #AirbnbHost #STRLoophole #WealthBuilding #MavenCostSegregation

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Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show!

Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide.

💡 Tired of losing revenue to Airbnb and Vrbo? What if you could connect directly with guests and keep more of your profits?

Today, we sit down with Eric Goldreyer, CEO and founder of Savvy, to explore the future of direct bookings in vacation rentals. Eric shares how Savvy’s book-direct marketplace empowers property managers to connect travelers straight to professionally managed properties—often saving guests 15–20% compared to traditional OTAs.

We dive into why owning the guest relationship is crucial, how technology should enhance rather than replace hospitality, and what property managers need—like solid websites, PMS integrations, and trust-building tools—to grow their direct booking share.

If you’re serious about boosting profitability and reducing dependence on OTAs, this episode gives a practical, insider look at where the industry is headed and how to get ahead of the curve.

🎧 Tune in and discover actionable strategies to take control of your bookings and maximize your rental income!

Things we discussed in this episode:

1. What Savvy Is – Book-direct vacation rental marketplace.
2. Guest Savings – Guests save ~15–20% per stay.
3. Direct Connection – Guests contact managers directly.
4. Own the Relationship – Managers keep guest data and terms.
5. OTA Limitations – Hard to reward repeat guests on Airbnb.
6. How Savvy Makes Money – Free listings, paid boosted exposure.
7. Platform Scale – Thousands of managers, 150k+ properties.
8. Direct Booking Trend – More share shifting away from OTAs.
9. Direct-Ready Setup – Need good site, photos, PMS, booking engine.
10. Pros Only Inventory – Only professionally managed properties listed.

Get in touch with ERIC:

Facebook - ⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/savvystays

Instagram - https://www.instagram.com/savvy_stay

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.savvy.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #DirectBookings #VacationRentals #STRHosts #PropertyManagement #BookDirect #AirbnbHosts #Vrbo #HospitalityIndustry #SavvyTravel

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Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show!

Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide.

What happens when a lifelong teacher realizes the classroom isn’t the only place she can make an impact?

Today we sit down with Colleen Coale, co-founder of Hurford Place Hospitality, to unpack her journey from elementary school teacher to running 90% of a fast-growing short-term rental management company in Pennsylvania’s Pocono Mountains. Colleen shares the mindset shift that moved her from “I’m just a teacher” to confident business owner, how joining a mastermind changed everything, and why it took nine months of persistence to land her very first client.

We dig into how community and education fueled her growth from one property to ten, what it’s really like building a values-driven business alongside her husband, and the deeply personal motivation behind her mission to create inclusive, ADA-friendly vacation homes. This is a candid conversation about identity, grit, and redefining success—on your own terms.

Things we discussed in this episode:

1. 1. 1. Colleen’s shift from elementary school teacher to STR business owner.
      2. Jason’s own “chapter two” from media to short‑term rentals.
      3. What Hereford Place Hospitality does in the Poconos market.
      4. Colleen’s early doubts about masterminds and STR education costs.
      5. How the mastermind community provided support and first leads.
      6. The long ramp-up: nine months to their first management client.
      7. Their “ideal” owners: nervous, first‑time buyers who need guidance.
      8. Cleaners and local teams as major referral sources.
      9. The realities of building a business with a spouse.
      10. Colleen’s mission to create ADA‑friendly, accessible vacation homes.

Get in touch with COLLEEN:

Facebook - ⁠⁠⁠⁠⁠⁠⁠https://www.facebook.com/profile.php?id=61553603442076

Website - ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://hurfordplacehospitality.com/

#SmartStayShow #realestate #realestateinvestor #realestateagent #RealEstateInvesting #ShortTermRentals #AirbnbHost #STRBusiness #FemaleFounders #CareerPivot #HospitalityBusiness #MastermindGroup #AccessibleTravel #ADAFriendly

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Join Jason Muth of Prideaway Stays and Straightforward Short-Term Rentals and Real Estate Attorney / Broker Rory Gill for the first episode of SmartStay Show!

Following and subscribing to SmartStay Show not only ensures that you'll get instant updates whenever we release a new episode, but it also helps us reach more people who could benefit from the valuable content that we provide.