Locations that are a 0-1 hour car ride from san juan to a nice town/city with more affordable areas walking distance to the beach would be interesting as well. 

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

If it provides a nice return on investment and you plan to hold it for a long while, then it makes sense.I already talked to the city and its OK to do what I am describing. 

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. 

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

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. 

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

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

Augustine city limits?

@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!)