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

That could mean fewer lending regulations overall, which would be amazing.

It's important to stay informed about developments in the areas you're considering, as well as any potential changes in regulations or economic conditions.

And the locals in Highlands have been fiercely debating STR's and regulations for the last few years, so I wouldn't be comfortable buying there.

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

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 the last 18 months various states have instituted new rules, regulations or laws related to (1) need for licensure to wholesale (2) restrictions on marketing of a property in which you do not have ownership and (3) disclosure requirements when dealing with a homeowner that makes it clear to the homeowner that the contact signed with the wholesaler is not a definitive “sales” contract, therefore making it less likely home owners will sign4.

Personally, after working with numerous property managers in Las Vegas, I only trust two to handle this task for my properties.Compliance Is ComplicatedProperty management involves navigating a maze of city, state, and federal regulations.

Something has to get better in that market as the regulations are too confining and essentially up to interpretation by the city explore you engage with.

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