If it’s lawsuit protection you have to make sure you have nothing to do with how the rental is run, or you’ll be sued personally.

Is this a legit lawsuit I could bring against him?

I spoke with someone at the Village and they said there were no laws or ordinances for short term rentals yet and that they were "waiting to see what Chicago does" as I know there are some lawsuits being worked out in court and they expect that Chicago will come up with blanket rules for Cook maybe? 

For example: MIL/Mother in Law Suite)

For example, this one with in-law suite in San Jose is selling for over $3M and the in-law suite is the selling point: https://www.redfin.com/CA/San-...

Purchase price: $440,000 Cash invested: $17,000 Bought as a primary residence, now kids are grown up so currently renting basement and Mother in Law suit.

(Read lawsuit waiting to happen, if it is power). 

When we bought our house about four years ago, we considered the “ mother in law suite “ of no value and in the way.

She has been house hacking by renting out a mother-in-law suite on AirBnB. 

And the real protection comes from paying an attorney to defend the LLC's (and you) in a lawsuit.What is the cost of that, and the cost to get you released from the lawsuit personally because plaintiffs councils in some areas seem to like to generate (excess) fees with this maneuver?