The level of difficulty in hosting will go up 1000 fold. Currently a lawyer from keepchicagolivable.com/lawsuit filed a lawsuit against the city because the ordinance is beyond achievable. If it wasn't for the lawsuit, the ordinance would have went into effect a couple of days ago. Thats the good news. Some of my associates that I know have incurred fines from the city based on commercial fines...not residential. In every case that i know with regards to other hosts and our own experience is that if there is a 'complaint' either real or unreal, the city's way of 'dealing' with the host is to send out a 'building inspector'. You are under NO obligation to let that person in your home without a court order. They claim they only want to inspect the property because of a complaint. But its a ruse. Once they get in, the violations based on the ordinance can create such a headache that you could end up bankrupt. One stated that the violations weren't your ordinary residential violations but that of which they would place on your home as if you are a commercial building or hotel. My girlfriend didn't even see a judge but was rangled into going to court because a neighbor didn't want an airbnb on her block. She was so afraid that she paid the $1,000 (originally $1,500) fine just so that she could say she won't 'do it again'. I have a story that range right up there to where the city tried to take the house after a 30 minute inspection. It was on youtube but now that case is in federal court as well. They came in illegal into her locked property.
Instruct all of your guest to be discreet and inform them to not open the door for anyone...no police, no inspector. They are suppose to send you something in the mail and you have 180 days to respond before they can come into your place. Anything other than that is illegal.
