03 - Florida Bust: From Lost Disney Dreams to Real Estate Reality

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One more stop…

In our previous post, we shared our terrible attempt to purchase a condo in the Florida Panhandle. We were so unprepared…and we didn’t deserve to win the home we bid on. We just had a wad of cash and a desire to own a home in an area we knew we loved. It was obvious why the house we bid on sold so quickly. It was a unicorn. It was undervalued, and it was in a popular little beach town. The search for anything comparable was heartbreaking, and we soon realized our dream for the beach had to be put on hold.

๐Ÿฐ Part I: Disney Dreams and the Search for STR Gold ๐ŸŒŸ

Our family loves the full Disney experience, and we decided that owning a rental in the Orlando area could provide some decent rental income. It could also be somewhere we could enjoy with our 6-year-old daughter occasionally. We started to get excited at the idea of finding our own place in Orlando. We extended our pre-approval, and contacted a few different real estate companies. We were paired with a nice agent in the area that started sending us daily emails with listings in the MLS.

๐Ÿ๏ธ Part II: The Letdown in a Sea of Poorly Managed STRs ๐Ÿ๏ธ

We rented an AirBnb really close to all the parks, and planned a family vacation around the search for a rental home of our own. But as we delved deeper, we quickly realized that the highly regulated short-term rental market in this coveted region presented a unique set of challenges. The dream of finding a gem for a reasonable price faded quickly. We discovered a sea of poorly managed STR properties, often listed at inflated prices. It was disheartening to see many owners neglecting the quality and upkeep of their rentals. On the other extreme we saw large new neighborhoods being built with the sole purpose of running a short term rental community. They felt cheap and poorly constructed. I called them Amazon homes... We just kept striking out...

The letdown was palpable, and we faced a dilemma. Should we settle for a property that didn't meet our standards and risk becoming part of the problem, or should we pivot and explore new avenues?

๐ŸšŒ Part III: A Detour into the World of RVs ๐ŸšŒ

Frustration and disappointment can sometimes lead to unexpected decisions. Feeling overwhelmed by the challenges of buying our way into the STR market, we considered a different adventure (or mistake) altogether—buying an RV. The idea of hitting the open road and exploring the country was enticing.

However, after careful consideration, and spending dozens of hours climbing in and out of RVs all over Virginia, we realized that we hadn't exhausted our potential in the world of short-term rentals. Instead of giving up, we decided to take a different approach. We committed to thoroughly understanding our chosen markets, analyzing data, and learning the true value of properties. It was time to get serious and strategic.

๐Ÿ“š Part IV: A Fresh Perspective and Renewed Focus Discovering a World of Knowledge ๐Ÿ“š

As we refocused our efforts on the short-term rental market, we embarked on a journey of discovery. We immersed ourselves in the world of real estate investing, seeking out knowledge and insights from experts and experienced professionals.

One of our most valuable discoveries was Robert Kiyosaki's book Rich Dad Poor Dad. This groundbreaking work revolutionized our understanding of wealth creation and the power of real estate. Kiyosaki's teachings emphasized the importance of acquiring assets that generate passive income, and short-term rentals fit that bill perfectly.

Another invaluable resource was the Bigger Pockets community. This online forum is a treasure trove of knowledge and support for real estate investors of all levels. We tapped into the collective wisdom of the Bigger Pockets community to learn about different markets, financing options, and property management strategies.

Finally, we began to unlock the power of internet tools to research markets and identify potential investment properties. We used websites like Zillow, Trulia, and AirDNA to track market trends and compare rental rates. We also joined local real estate investor groups to connect with other investors and learn about new opportunities.

Through our research and learning, we developed a deep understanding of the short-term rental market. We gained insights into the factors that contribute to a successful investment, from choosing the right property to managing it effectively.

Armed with this newfound knowledge, we were ready to take our next steps and pursue our real estate dreams.


Jesse and Angie Ferguson