It should be noted that wholesaling has been regulated pretty strictly in Pennsylvania and wholesalers have to have a real estate license now among other things so there's likely less wholesaling going on in Philadelphia as in other places. https://consolematison.com/2024/06/12/new-legislation-on-res...

@Belinda Fello- Usually, when you rent a property that has an HOA, you have a term in your lease that requires the tenant to comply with any rules or regulations of the HOA. 

A heavily regulated market.

I understand each city/county may have their own permitting requirements, fees, regulations, etc. but I'm wondering how people are making any return on their investment if it maxes out at 90 day rental.

The City does not currently have regulations or allowances for land use known as “short-term rental.”

Are there any local regulations or processes that are particularly tricky to navigate?

If you are in a metro area, I would always make sure it works as a LTR as a worst case scenario that regulation shifts.

Personal residences or properties primarily held for personal use typically don't qualify for a 1031 exchange.Understanding state-specific regulations for like-kind exchanges is crucial.

New airbnb regulations obviously, but anything else? 

Lastly, don't overlook any local regulations or HOA restrictions if any.