More then willing to share what we have learnt and why these  cities with anyone who wants to chat

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

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

Cities and states have enforced this policy for well over 50 years and it always stood up in court.

Detroit is just like any other Midwestern rust belt city.

That is on one of the largest arterial streets in the city, massive traffic count.

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. 

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. 

Here is a video that runs down the basics - https://s-media.nyc.gov/agencies/specialenforcement/01-Legal...There is also a prohibited building list - https://www.nyc.gov/site/specialenforcement/registration-law...Here are some more info overall - https://www.nyc.gov/site/specialenforcement/registration-law..All of this makes STRs in the city pretty tough but it certainly not impossible.

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