Would love to know how others here approach this.

Challenges?

That's one approach at least.  

As many of you know, finding a condo building that permits short-term rentals in Chicago is extremely challenging due to HOA and city restrictions.I just pulled data on a handful of active condo listings where the buildings explicitly allow short-term/Airbnb rentals.

What challenges or questions are you running into?

Both renters describe themselves as clean, but their habits have been challenging to manage.

Challenges?

Out of state is more challenging than as it's been presented. 

I want to set things up correctly from both a liability protection and tax-efficiency standpoint but I’m not sure what the smartest approach is.I want to make sure I’m protected personally, while not overcomplicating things or eating up profits with unnecessary entity costs.If anyone has been through a similar situation—owning properties in more than one state—and can share what structure worked well (or what to avoid), I’d really appreciate the insights.Thanks in advance!

As colder weather approaches, I make it a priority to stay informed about weather conditions and plan accordingly.