Calling All Florida Market Experts!

[Adam Tafel]

I've been toying with the idea of buying a winter getaway home, one I could rent out Airbnb/VRBO April-November. I live in St. Paul, Minnesota where I have a great career, investment properties, and a small vacation-rental business. I love it here, but winters kill me. I've been tempted by homes in Vieques, Puerto Rico and Costa Rica, but I'm considering all options. I keep running into friends, family, and coworkers who are raving about certain areas of Florida, and I thought posting on here would be the most efficient way to get some opinions. I'm an agent, and could probably drum up some business in the winter months while I'm down there. 

Things to consider:

-I need to be in a city, walking distance to a business district of some kind

-I'd like to follow a path of progress within a city, and don't mind being close to (but not within) sketchier areas

-a market where the average 3 bed 2 bath sells for under *ideally* 250k, but up to 350k (I'll be looking for a property that needs work, but this sort of market)

-must be SF no association

-I'm 31, single/no kids. Local culture is important to me.

Ok I think that's probably enough info- and yes, I realize it's a big state. I know nothing about it. I've been to Disney World as a kid, and I have layovers in Ft Lauderdale all the time. I appreciate any/all opinions and suggestions!