Sometimes, buying an existing property can be more cost-effective and less time-consuming and maybe require slightly less permits, etc. 

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). 

If you're going to do it alone, make sure you your due diligence: estoppels, inspection, review, consult with a local attorney familiar with the local regulations, etc. and good luck.

However, there is no specific holding period contained in the tax code or regulations and there is no "safe harbor." 

If the Owner wishes toterminate the agreement during an existing tenancy the owner will be held liable for payment ofmanagement fees for the duration of the existing lease as well as a $300 + GST cancelationfee.

One of the other factors that kept me from pulling the trigger is that the city has never passed any real STR regulation.

However, private financing options are becoming increasingly popular for scaling portfolios.Zoning and restrictions: As you mentioned, regulations for short-term rentals, such as Airbnb, vary significantly.

All of this said, be sure to do your research on STR regulations first and find a STR friendly location.

There are opportunities out there but some strategies are risky. 1 - Airbnb (STR) comes to mind - very competitive, very saturated and becoming highly regulated.2 - Most STRs are transitioning to MTR so that market will be saturated soon if it isn't already.3 - Insurance crisis in florida is getting bad so those costs will eat up cashflow and short term appreciation.

As long as there is no "healthcare" being provided (medicine, baths, etc) then it's not regulated by the department of health.