Pricing and risk levels are about the same for the same type of stuff in either city.

Hey @Mike Nelson, never assume anything about STR rules and regs.Here is the STR rules for Oak Park - https://codelibrary.amlegal.com/codes/oakparkil/latest/oakpa...I would call the city and make sure it is legal for a specific property.Now regarding the famous person angle, sure it can add value to the property or as a STR, but for STR use, I would think you would need it to be in original condition with a lot of the furniture and knick-knacks that were owned by the famous person along with a bunch of photos etc featuring the famous person.If you buy a place that has been totally redone but was owned by someone famous but has no features or things that were theirs, then I don't see it being a draw. 

I learned about the city over time and began my out-of-state investing journey. 

I've definitely made some mistakes here but I'm going to be very candid with the info on the deal, so please go easy on me haha.My brother and I purchased a property on a large lot in Culver City CA in 2020 that was essentially a tear down. 

Quote from @Ryan Brown: Your city has noise ordinances.

They couldn't get a construction loan and were constantly blaming the cities being tough on their permit process.

Cities and communities are also cracking down on people using homes for this.

@Kris Lou Many factors go into PMC pricing:1) Locality (city/state)2) Neighborhood & Property Class (time to manage Class A < Class B < Class C < Class D)3) Property condition (slumlord properties hard to manage)4) Number of units (some economies of scale, but not as much as owners think)5) Owner expectations (some owners really want a personal assistant!)

You can also use online resources such as City Data to search demographics in the area. 

Make sure to vet and look into multiple different PM's per city.