@Daisy RuizTo echo @Michael Baum, I have not seen or heard from many people operating STRs in Chicago.

If you're hoping to be a co-GP and learn to both operate and raise capital then I think investing money in a good education system is probably money well spent.  

Is that the case or is it  I'm wondering if you need it to be considered a separate dwelling by the city to operate just the basement as an STR?

These are professionals with additional training and a stricter code of ethics.

However to date I'm not aware of anyone operating here. 

@Anna Catron High leveraged operators have always been wiped out with enough time, I don't think that will change.

I find it easier to work with people and let them know the boundaries they have to operate in with their pets than to simply say no. 

Whether it's Airbnb, VRBO, FF, Zillow, FB, direct booking website, insurance relocation portals, databases from MTR operators who get a lot of insurance/corporate leads, CHBO, etc.The MTR space is still quite young, unlike STR. 

Ultimately it may be too pricey for them but they've already moved in, I'd ride that train until they got there.

Supply and demand drives the train.