Great idea, but check your local regulations.

I'm looking to buy a house in the St Pete market & have read zoning regulations, articles about STR (anything less than 30 days) and have discussed with my realtor.  

Understand Chicago ZoningChicago’s zoning regulations vary by ward.

Remember your situation is unique so it's important to consult with a tax advisor or CPA to explore all available options and ensure compliance with tax regulations.

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

I’m not sure all of the regulations/rules to this in PA though.

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). 

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

Consult a CPA or real estate attorney to understand tax implications, build a reserve fund for unexpected costs, and research local regulations to ensure a smooth and profitable transition into rental property ownership.Good luck!

I don't see them ever reversing the regulations.