Sister: Wants to make sure her parents are not taken advantage of.

Quote from @Sherry McQuage: Make sure to check the zoning to make sure mobile homes are permitted there; check for any hazardous waste designation for the area; will you need to have the parcels surveyed out in order to sell the size you intend? 

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. 

Keeping the good relationship with her and thus your grandkids is more important that the rest of it so make sure you are prepared to give and sacrifice money if and when it is required and have certain things agreed up and in writing up front.

Make sure your address falls under that range. 

We use Hiscox for our insurance with our business, not sure if it works for property but its worth a try. 

That is part of the reason I'm not sure it matters as much whether I am in my home market or not - other than the fact that I have greater knowledge of the local market. 

Make sure to have some good cleaners, not just one, but a few. 

Not sure if your property is in that area as you are a bit West.

There are surely STR Facebook groups for this location.