My understanding is the TN has some crazy rules and regulations that complicate this process.

Trump did not address housing as directly but has previously suggested cutting regulations and using federal land for new construction.Sharing this because it could have a significant impact on the housing market in the near and long term. 

Here are 2 articles talking about new regulations they're trying to put on STRs there, which definitely could impact your rental income, especially if you buy in an R-1 area. 

Compliance issues regarding local landlord regulations not an issue in my area.

Colorado is quickly becoming on par or maybe even worse than California as far as landlord/tenant regulations. 

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. 

In making this determination, the enforcement agency shall consult with the entity responsible for enforcement of building standards and other regulations of the State Fire Marshal pursuant to Section 13146.(4) The enforcement agency shall not approve any applications pursuant to this section on or after January 1, 2030.

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.

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