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

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?

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

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. 

"Seller" allowed a syndicator to "buy" the deal by paying "seller" presumably a lot of money and an agreement to take over all operations.  

There are also additional costs of operating and maintaining an LLC, like separate bank accounts, annual report filings, tax filings, etc.2.

Please don't reply with, "I want an operating loss to offset my income."

It also is helpful to have a California LLC in case you ever sell that property and move into another state so that you do not need to form a new LLC altogether with new operating agreement, just re-register in the new state as a new foreign LLC.

Most of the time you'll be fine, but when something bad eventually happens (with enough exposure over time, you are virtually guaranteed to have something bad happen), the outcome is likely to be catastrophic.