The area has certain advantages like shelter from regulation risk (pretty much as low as anywhere in the country if you buy in the approved STR tourist zones) and long term security (people aren't going to stop going to Orlando anytime soon). 

In some cases that's amazing -- one part of the town gov't considers it to be a commercial lodging establishment so it's exempt from STR permitting and regulation. 

The real skill is understanding the variability and risk in each number which is not always numerical or scientific.

These programs offer options for less money down and in some cases DPA - Down payment assistance.As a banker for over 18+ years I am very skeptical when I hear a new name in the business only because its become tougher to lend with all of the new laws and credit/insurance requirements and regulations.  

No, it is inside of an HOA neighborhood but the current regulations only restrict rentals under 30 days stays.

Search the BP for ADU appraisals to encounter numerous examples.

TD and Congress needs to come up with more relaxed tax regulations to make investing in real estate lucrative again.

Start by researching local regulations and working with an agent experienced in vacation rentals.

Once you hit a certain number of loans (check with your state dept of banking and finance or dept of business regulation), they might require you to have a license.

Known  Potential Black Swan events, numerous.