3) Where can I find accurate market data such as school system ratings, population growth, median household income, and crime rates for specific neighborhoods in Orlando?

It's a bit of a quiet area but local people may find a STR of interest there.

Mathew, From my perspective you need to talk with local real estate investors and a quality realtor to determine what is needed as well as paint choice options.

Once you get closer to making the move, reach out to local agents to get up-to-date info from the MLS.

My go-to with smaller value properties is a commercial loan, which usually is based on either 15% or 20% down and my favorite lender locally for this is currently between 5%-6% depending on the rate-lock period (between 3-10 years) and the loan is amortized over 20 years.That's my go-to strategy. 

Start saving money, work on your credit score, get approval for loans ahead of time, and meet and talk to local real estate sellers, other investors, and people who manage properties.

Also, are you local to either market? 

I would pass your scenario by a local CPA to cover your bases.

To me this includes being members of your local REIAs. 

Best in the game, better than Navy.Try local community bank or credit union for investment properties.