It's definitely recommended to get permits if you have not.

Florida definitely seems to be booming these days

NC and SC have some great markets for short term rentals and you would definitely increase your wealth by splitting the money and buying multiple properties.

You should definitely consult with a local eviction attorney throughout the process.

I can't tell you how many times I've gone to the property and it is gone, or you figure out something is wrong, maybe the legal description, or the address, or there is $100,000 worth of junk there you need to haul off that was not in the pictures, or that cool commercial building, that when you get there has the faint words that you can now make out to be a former dry cleaner, or gas stations, or lead smelter, or oil change shop or something like that. 

***This is not legal of advice.

All strongly appeciating neighborhoods, but can be a rough tenant base.A rent by the room situation (renting our basement if it is legal living space) could be a good solution in Brightwood or Riggs Park...or even Silver Spring.

It can definitely be worth it to push it to its limit the first property or two.

Smartland's property management has definitely surpassed my expectations too.

In all sincerity I think you're going to have to find what checks all of your boxes.If you're going to buy and hold, value add is definitely a strong play.