Thanks, Devin. From what I understand Venice is relatively easy to work in, same for Sarasota. A bit further north (clearwater, st pete) seem to have some strict STR regulations. Also, I won't buy in a HOA or community....currently trying to get rid of a place in the Poconos (PA) because of how poorly they operate (getting a speeding ticket for 23 in a 20mph while neighbors have 8 broken down cars on the front lawn).
So, I find myself with these options;
1 - Buy a single family philly row home in a nice neighborhood (prices still good) and use it as a traditional rental. With this plan, I can also pay down about 80% of my primary residence (possibly all of it) and have no mortgage on that. While I'm not a huge fan of renting out single-family homes, the row houses I'm looking at are 800-1000 sq ft, small, contained, mostly updated, high likelihood of appreciation and stable rental area.
2 - Buy a duplex in Philly for a traditional rental. Have a little money left over for cushion/projects.
3 - Buy a house in Florida to use as a vacation rental. This is the plan that I get eager about, but it's also a big gamble in my opinion.