02 - Lessons Learned: Selling a Long-Term Rental and the Florida Panhandle Bidding War

  • Posted on


How did we get here? 

In our previous blog post, we shared our journey into the short-term rental market, highlighting the reasons that drove us to make that life-altering decision. Now, we'd like to take you through a pivotal chapter in our story—a moment of reflection, realization, and resilience.


Part I: Letting Go of a Liability


Before our successful foray into short-term rentals, we encountered a challenging situation that taught us a valuable lesson. I previously owned a long-term rental property that, over time, began to feel more like a liability than an asset.


The property was in an excellent rental area. I had purchased it before I met Angie, and held onto it as we settled down to start a family. It was in a reliable market, and I had a very aggressive property manager that kept excellent tenants under contract. But the house demanded constant maintenance, the HOA was poorly managed and grossly in debt, and the rental income barely covered the costs. It was just leaving us with a financial burden rather than the ever desirable passive income. It became clear that we faced a tough decision: to continue with a property that drained our resources or to let it go.


In August of 2019, we chose to sell the home to the tenants. They had expressed interest in purchasing the home several times. They loved the house and were excited to make it their own. It was a challenging decision, but it freed up both our time and finances, allowing us to refocus our efforts on different investments—But what investments?


Part II: Now what? August 2020


By this time, we had paid down a significant amount of debt, and flipped our mindset about money. We knew spending our money to purchase assets, rather than wasting it on liabilities was our next move. We spent almost every night shuffling through business strategies. We spent countless hours researching franchise opportunities ranging from Crumbl Cookie to Crossfit Gyms. We even considered Off Road Adventure companies and car washes. We knew we had an entrepreneurial bug but we struggled to find what would fit with our lives as regular W2 workers.


Then we rented a cabin and had a week of absolute bliss in the Smoky Mountains. We spent every night swinging on a porch looking over some of the most beautiful landscape in the county asking ourselves “How? How do people buy these houses and rent them out?” We asked ourselves “How can they afford it?” And then it clicked…sort of. For the next 6 months, we spent every night researching beachfront markets from Maine to the Florida Keys. We were going to buy an Airbnb.


Part III: Okaloosa Island Out-Bid


The Florida Panhandle captured my heart in 1996 while visiting a military buddy who lived in Fort Walton Beach. I immediately fell in love with its white sand beaches, crystal-clear waters, vibrant tourist scene, and a laid back approach to life.  I swore to purchase a home there one day.


Then in March of 2021, while scrolling through the daily MLS, Realtor.com, and Zillow listings, we found the perfect deal. A modern, beachfront, one-bedroom condo that needed minimal updates and low maintenance fees. It had beach access, and a pool, and it was oozing with rental potential. It was literally EVERYTHING we thought we were looking for.


With excitement in our hearts, we picked up the phone and called our realtor and submitted a very competitive bid on the property. But we didn’t even have a pre-approval yet. We just assumed our credit was good, and as far as we knew, the bid we made seemed within our budgetary reach. Sadly…or maybe fortunately…within just a few hours of our bid, we received the shocking news—someone made a cash offer well above the asking price.


The disappointment was palpable. But the first lesson we learned was that we had no idea what we were doing. But we knew we needed to be prepared to act swiftly and strategically in the face of stiff competition moving forward. Our journey into the short-term rental market was not to begin on the shores of Destin.

Please keep checking back for updates. We will continue our story with the second attempt to enter the desirable market of Florida. We have load of ideas, and I am continuing to update this site, and the future of JAC Rentals. We hope you enjoy

Jesse and Angie Ferguson