The Cycling Mermaid

[Tara Jenkins]

Investment Info:

Single-family residence buy & hold investment.

Purchase price: $530,000
Cash invested: $100,000

My journey into short-term rentals began after years of investing in long-term properties, but it was a podcast that opened my eyes to the incredible potential returns of STRs. With my background in hospitality and a drive to create exceptional guest experiences, I decided to take the leap. I partnered with an experienced STR agent, Troy Nowak, and purchased my first short-term rental in Palm Harbor at the height of the real estate frenzy, navigating fierce competition and ultimately overcoming

What made you interested in investing in this type of deal?

After being outbid multiple times in the Smoky Mountains, I took Brandon Turner’s advice to heart when he said, "Where do you have an unfair advantage?" That’s when I realized I already had a strong connection to the Tampa Bay area—my aunts and uncles live in Largo, just 30 minutes from this home. Having local family gave me a built-in support system, market familiarity, and the confidence to manage a property from a distance if needed.

How did you find this deal and how did you negotiate it?

I worked with an expert STR agent, Troy Nowak, who guided me through the purchase and negotiation process. Given the competitive market at the time, every property was receiving multiple offers, and securing a deal required both strategy and speed. Troy helped me identify properties with strong short-term rental potential, and when we found this home in Palm Harbor, we moved quickly to make a competitive offer. Despite facing an unexpected $30K appraisal gap.

How did you finance this deal?

I used a HELOC to cover the down payment, appraisal gap, and furniture, allowing me to enter the STR market without depleting cash reserves. While the appraisal gap was a hurdle, I saw the long-term potential and moved forward. Thanks to strong bookings and smart management, I recently paid off the entire HELOC!

How did you add value to the deal?

I added value through great management and a focus on delivering an exceptional guest experience. By prioritizing five-star reviews, I built a strong reputation, which led to increased bookings and higher profitability. Quality furnishings, attention to detail, and seamless operations helped set the property apart, maximizing its earning potential.

What was the outcome?

The outcome was a beautifully furnished home in a prime location with a low mortgage that generates consistent cash flow. Not only is it a profitable investment, but it’s also a place my family can enjoy for years to come. This deal proved to be the perfect balance of financial gain and personal enjoyment.

Lessons learned? Challenges?

I quickly learned that pools are expensive to maintain, but they’re also a major draw for guests. Anticipating guest needs is key to securing great reviews and repeat bookings. The market is competitive, so I focused on being the best—from high-quality furnishings to top-tier management. Every challenge taught me how to refine my processes and maximize both guest satisfaction and profitability.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

Yes! I worked with Troy Nowak, an expert STR agent who guided me through the purchase and negotiations. His knowledge of the short-term rental market was invaluable in securing the right property. I also worked with a great lender who helped navigate financing options, including my HELOC, to make the deal happen. I highly recommend working with professionals who understand the unique needs of STR investors—it makes all the difference!