You can sidestep most of the headaches if you stick to these five golden rules:- Know Your Market Inside OutTake time to research neighborhoods, property values, and what buyers are looking for.

However, make sure to research thoroughly—there are many providers in the market, but not all have the experience or track record you’d want.For consistent cash flow and long-term appreciation, look into areas in the Southeast.

One means of research: talk to an experienced real estate agent that specializes in work with investors. 

It's the sort of market that passes every metric or test when you start doing research, though. 

Research competition  and determine their profitability and how much they spend on marketing, how many employees they need, and how much time the wholesaler needs to devote to the business.  

From my research so far, it seems the demand is pretty high in general for STR's, I was also looking at San Antonio but would prefer to be in Florida and Jacksonville is the city in Florida that fits my budget, interested to hear from anyone who may know more about STR's there and to connect with anyone.

I live in Tampa FL and housing prices are ridiculously expensive and from a basic research I’m pretty sure I could build cheaper.

As such my market research is based on longterm rental criteria.

I would pick a major tourist destination where it wasn't saturated with STR's already.That would take some research but you could google top vacation destinations and find a place you would go on vacation.

Quote from @Marcus Auerbach: I've researched this and I believe it's vague on purpose.