@Christian Artuso - check out the straight up Chicago investor page for events in Chicago.

Once Apartments.com is going the money comes without much thought. i check on the first to see that the transaction has initiated then again on the eighth to see that the money deposited.

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).  

Check out the Short-term and Vacation Rentals forum.

If PropStream’s data isn’t cutting it, you might want to check out Prime Tracers.

AS we see some GP failures there is another thread on this guy Lane Kawauka not sure how you spell it but one of his investors gets on BP and says they go dark..

They paired me up with a member service advisor for 60 days, who checks in on you once a week and helps find content for you and keeps you accountable.

So you need to check with the zoning department about non-owner occupied and how hard it is to get the variance.

Be sure to check out the free tools BP provides to help analyze deals you may have and also market insights.

Im not an STR SME - I would check with Mike Savage and Dan Rivers - theyre the local experts on STRs.