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...

The company doesn't really have a "credit score" or "eviction history" so I'm thinking about asking for 1.5x or 2x monthly rent as a deposit (we normally do 1x month rent) just like I would for a tenant without established credit history.Thanks!

@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. 

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.

A heavily regulated market.

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?

Once you've established yourself as a thought leader and built a solid reputation, it's time to unleash your investment opportunities upon your trusty investor list.

I just shy away from places without strong established tourism markets i.e. growing urban areas, national parks, beaches etc.

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.