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 wish you would have told us the year, it makes a huge difference.Anyway, everything you mention, plus 1) get a camera run on the sewer line, 2) make sure the Elec panel is newer and sized correctly (a lot of HIs will just say if it's functional or not) 3) Foundation ( is it slab or raised?)

I want to make sure I am putting my best foot forward with this guy so I was hoping for some examples and feedback here.Let me know!

What we are working on is making sure that the business is organized and prepared.

High property prices mean fewer people can afford to buy, so more people rent.

Even if the rental has a decent cash flow with additional flood insurance, we're still not sure we want to take on that risk as we are out-of-state investors (planning to move back to KY in the future, but not now) and we don't like that it will potentially bring down the perceived value when we try to sell it in the future.The seller has never lived there and has not provided any information on if it has flooded before or not. 

Quote from @Kristian Forbes: I'm not too sure yet.

Southwestern Michigan offers plenty of charm and is a destination place but would definitely make sure your ROI makes sense based on your long- and short-term goals with the property.

Since it was a structural change, you need an architect or engineer to draw up plans that make sure the new changes are safe of course. 

I would love a calculator that could help me make better decisions but not sure that exists.