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 document my inspection with photos so the condition is recorded from that point forward.

Are their listings detailed with good quality photos?

I’m curious about your property type, amenities, photos, and reviews etc.

@Nichole StohlerI find using a SDIRA to be a great tool for passive investments and growing your retirement with less stress than the stock market roller coaster. 

It's likely a scam anytime they sound like AI or the grammar is weird or they use the word "kindly", if they ask for you to respond to them off-platform, if they say their employer will pay for it, if they ask if the dates they've specified are still open (when they can clearly see they are open on your calendar), if they ask for a video of your property (they probably want to set up a duplicate listing with your photos and video and scam others out of money), or if they want a long term booking and they have just joined the platform and have no reviews (could have been evicted from somewhere else, and hope a newbie will let them in with no background check, they'll end up not paying or credit card is bad).  

In fact, given current boom in Stock market, one is way better off investing there.

If you like to be risky with your capital maybe try putting it in some index funds, crypto, or stocks that you believe in and understand and then take it out when its made a good return and then use it for the downpayment.  

You need a repair partner who can get out immediately and has quick access to replacement parts (if not already in stock). 

With 56% appreciation rates in less than 10 years, even the stock market can't beat North Carolina!