Building a Short-Term Rental Portfolio from Scratch

Short-term rentals offer incredible opportunities for building wealth, as Travis and Regan Perry have proven.

The Iowa-based couple turned a simple idea into a flourishing portfolio of short-term rentals across multiple states. Here’s their story.

From Humble Beginnings to a Booming Business

Travis and Regan’s journey began modestly.

While Travis was wrapping up his football career at the University of Iowa, he started studying wealth-building.

Inspired by the financial success of real estate investors, the couple purchased their first property with the intention of turning it into a rental.

What started as a single condo evolved into a portfolio of eight properties in five states, including Iowa, Michigan, Utah, Colorado, and Missouri. Their strategy? Live in a property, rent it out for short-term events like football weekends, and save the profits to fund their next investment. Over time, they transitioned from long-term rentals to short-term and midterm rentals, creating a sustainable business model.

Key Strategies for Scaling a Short-Term Rental Business

1. Strategic Market Selection
The Perrys focus on properties within a three-hour drive of major cities, ensuring consistent demand from weekend travelers. By targeting destinations like Southwest Michigan, which are easily accessible to large populations, they attract guests seeking convenience and unique experiences.

2. Leveraging Tax Benefits
Travis and Regan use cost segregation studies, bonus depreciation, and the STR strategy to optimize their tax situation. These strategies generate significant tax refunds, which they reinvest into new properties, accelerating their portfolio’s growth.

3. Prioritizing Unique Amenities
To stand out in competitive markets, the Perrys invest in features like game rooms, murals, hot tubs, and saunas.

They analyze local listings to identify gaps and exceed guest expectations, ensuring high occupancy rates and glowing reviews.

Overcoming Challenges in Short-Term Rentals

Navigating Regulations
The couple emphasizes the importance of researching local laws and attending city or township meetings to understand potential regulatory risks. They also build relationships with neighbors to ensure smooth operations and address concerns proactively.

Managing Remotely
With properties in multiple states, the Perrys rely on strong local teams and technology. They hire reliable cleaners and handymen through Facebook groups and local networks, and they maintain a list of backup providers. Tools like PriceLabs for dynamic pricing, smart locks for guest access, and HostAway for property management streamline operations.

Meeting Material Participation Requirements
By tracking their time meticulously using tools like RepsTracker, Travis and Regan consistently meet material participation requirements for tax benefits. From property setups to guest communication, they log hundreds of hours annually.

Balancing Family and Business
Regan left her teaching job to manage the business full-time, allowing the family to scale faster while caring for their three young children. The division of labor plays to their strengths: Regan oversees operations and guest relations, while Travis continues working in commercial real estate, leveraging his expertise to analyze deals and manage finances.

Expanding into Consulting and Co-Hosting
As experienced investors, the Perrys now help others succeed in the short-term rental space. Through their website, ShortTermRentalEdge.com, they offer consulting, property setup, and co-hosting services. They also provide free resources like inventory checklists and blog posts for aspiring hosts.

Top Advice for Aspiring Investors

• Build a Reliable Team: People come before profits. Take care of your cleaners, handymen, and neighbors to ensure smooth operations and longevity.
• Stand Out: Invest in unique amenities that create memorable guest experiences.
• Do Your Research: Vet regulations and market demand thoroughly before purchasing a property.
• Document Hours: Keep detailed records to meet tax requirements and maximize benefits.

The Future of the Perry Portfolio

Looking ahead, the Perrys plan to diversify their portfolio with more midterm rentals while continuing to expand in high-demand markets.

Their approach—combining strategic investments with operational excellence—shows that success in short-term rentals is achievable with the right planning and commitment.

Whether you’re just starting out or looking to scale, Travis and Regan’s story is a testament to the power of persistence, teamwork, and smart strategies.

If you’re looking for tailored short-term rental tax strategies, schedule a free consultation with our team.

Transcript

Intro: 0:00 – 0:03

Ryan Carriere, CPA:
Welcome, Travis and Regan! Thanks for joining us. For listeners, Alex Savage is stepping in as co-host today. Let’s start with your story—can you share your background and how you got into short-term rentals?

Journey into Real Estate: 0:03 – 2:41

Travis Perry:
Thanks, Ryan and Alex! We’re big fans of the podcast. We live in Tiffin, Iowa, just outside Iowa City. It’s a fast-growing town, and we have three young kids who keep us busy.

I started exploring real estate when my football career at the University of Iowa ended. I wasn’t sure about my next step, so I immersed myself in books, podcasts, and articles on wealth-building. It became clear that real estate was a common thread among successful individuals. Early in our relationship, I told Regan I wanted real estate to be part of our financial strategy.

Our first property was a three-bedroom, two-bath condo, which we lived in for a year before renting it out. Over the years, we added more properties, starting with long-term rentals and eventually transitioning to short-term and midterm rentals. A pivotal moment came when I met the CEO of Rent Like a Champion, a company focused on short-term rentals near college campuses. Inspired, we rented our home during football weekends, earning enough in seven weekends to cover nine months of our mortgage.

Transition to Short-Term Rentals: 2:41 – 6:57

Regan Perry:
After turning our condo into a rental, we bought a townhouse, followed by a duplex, always with the intention of renting them out after living there briefly. Eventually, we moved into a single-family home and started renting it out during football weekends and for other events like weddings and family visits. We realized the potential of short-term rentals and shifted our focus.

Despite initial hesitations—especially when I was pregnant—we even rented out our primary residence again in 2023. The income allowed us to take a vacation to California, which the rentals fully funded. Now, we’re dedicated to short-term and midterm rentals, though we’ve kept our first two properties as long-term rentals.

Scaling the Portfolio: 6:57 – 10:58

Travis Perry:
Over the years, we’ve added one short-term rental per year, growing to eight properties across five states. We also operate 11 rental arbitrage units for traveling nurses and manage other properties. We leverage cost segregation studies and bonus depreciation to maximize tax benefits, using the resulting refunds to fund new investments. This rinse-and-repeat strategy has helped us scale quickly while maintaining a diversified portfolio.

Alex Savage:
Your journey is inspiring. You’ve managed to scale while balancing a W2 job and family life. What states are you currently investing in?

Travis Perry:
We have properties in Iowa, Michigan, Minnesota, Missouri, Utah, and now Colorado. Our strategy focuses on properties within a three-hour drive of major cities like Chicago, to attract weekend travelers and vacationers.

Work-Life Balance and Transition: 10:58 – 13:48

Alex Savage:
Regan, you transitioned from teaching to managing properties full-time. What was that like?

Regan Perry:
Leaving teaching was bittersweet, but it made sense for our family. Travis continued his W2 job in commercial real estate while I took over managing our growing portfolio and caring for our kids. It was challenging initially, but it’s been incredibly rewarding.

Operational Tools and Efficiency: 13:48 – 20:15

Regan Perry:
Managing multiple properties requires efficiency. Here are our key strategies:

• Building a Team: Reliable cleaners and handymen are essential, especially for out-of-state properties. We find them through Facebook groups and by connecting with local Airbnb hosts.
• Documentation: We maintain master property documents with every detail, from HVAC contacts to lockbox codes.
• Tech Tools: Tools like PriceLabs for pricing, smart locks for guest access, and HostAway for property management simplify operations.

Ryan Carriere, CPA:
You’ve clearly built a solid system. How do you manage cleaners across multiple states?

Travis Perry:
We interview multiple cleaners during property setup and maintain backup contacts. Building strong relationships with neighbors has also been invaluable—they sometimes help with things like trash or minor issues.

Overcoming Challenges and Regulations: 20:15 – 24:57

Ryan Carriere, CPA:
How do you navigate regulatory challenges in different markets?

Travis Perry:
We research regulations extensively before investing. This includes reviewing local bylaws and reaching out to city councils and township boards. It’s critical to ensure short-term rentals are allowed and to anticipate potential future changes.

Achieving Material Participation: 24:57 – 27:29

Alex Savage:
Many investors struggle to meet material participation requirements for tax benefits. How do you manage it?

Regan Perry:
We document everything. Between property setups, guest communication, and regular visits, we accumulate 600-700 hours of participation annually. Tracking tools like RepsTracker make it easier to stay organized.

Tech and Automation Insights: 27:29 – 30:49

Ryan Carriere, CPA:
What tools do you use to predict revenue and streamline operations?

Travis Perry:
We start with AirDNA for market analysis, but we go deeper by reviewing local Airbnb listings and analyzing their performance. On the operations side, tools like smart locks and automated pricing systems save us significant time and effort.

Future Plans and Market Expansion: 30:49 – 35:38

Ryan Carriere, CPA:
What’s next for your portfolio?

Travis Perry:
We plan to diversify further by adding more midterm rentals and exploring new markets outside the Midwest. Our strategy remains focused on properties within driving distance of major cities for consistent demand.

Advice for Aspiring Investors: 35:38 – 39:18

Travis Perry:
Prioritize building a reliable team and planning for contingencies. People always come before profits. Take care of your cleaners, handymen, and neighbors—they are the backbone of your success.

Regan Perry:
Stand out by investing in unique amenities upfront. A great guest experience leads to better reviews and higher revenue.

Consulting and Co-Hosting Services: 39:18 – 42:00

Alex Savage:
You’re now offering consulting and co-hosting services. Can you share more?

Travis Perry:
We launched ShortTermRentalEdge.com to help others succeed in short-term rentals. We offer deal analysis, property setup, and management services. Our site also has free resources like inventory checklists and blog posts.

Regan Perry:
You can follow our properties and tips on Instagram at @PerryDiceVacationRentals.

Closing: 42:00

Ryan Carriere, CPA:
Thank you, Travis and Regan, for sharing your journey and strategies. Your insights are invaluable for investors looking to scale their short-term rental portfolios. Check the show notes for links to their website and resources. See you next time on the TaxSmart REI Podcast!

If you need help with tax planning, book a free consultation. If you’re a CPA or EA looking for a career change, reach out to us at onboarding@wholecpallc.com.

See you next week on the TaxSmart REI Podcast!

Disclaimer: This podcast summary and transcript were partly generated and may contain some errors or miss key points from the audio recording.