They financed 100% of that transaction, and I took on a huge loan - a huge risk for a broke guy like me.

As long as you're doing that, there's always a risk, and 50 years from now it will probably be illegal everywhere to operate STRs in residential zoning, just like it's illegal to operate a steel mill there. 

My recommendation would be to choose potential markets - in several price points - that have strong rental demand and year-over-year rent increases and that also are in markets that are appreciating. 

Best bet would be a “partnership” with a monied individual looking for a high risk/high return passive investment with you providing the “active” part.  

The risk increases the further you go from home, so I'd just stay home if I were you.

I am moving out to the Destin/Fort Walton Beach area at the beginning of next year in January for work. My goal is to buy a house in the area and house hack the remaining rooms. I am hoping to connect with other like-...

Our primary objective as coaches is to help clients ask the right questions, develop the right criteria, and identify potential red flags. 

The potential problems mentioned by the responding posters in this thread are real and well thought out.  

It was a risk but thankfully paid off for me.

@Kyle Cross, correct me if I'm wrong, but I think maybe what you're getting at is potentially pitching to your parents that you would like to take a shot at personally managing the units to gain experience and some form of compensation.