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.

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

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

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!

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.

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

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.

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.