Most cities do not allow "boarding houses" and/or have a "no brothel" law. 

@Mindy Rosscup, you want a contract that is specific to the laws of your state.

We are on all of the above, as well as:- Marriott Homes and Villas- Google Vacation Rentals- Jetblue Airlines- Allegiant Airlines- about 10+ more and soon to be American Express Travel and Hyatt's portal. 

Or else reduce enough on price to deal with an eviction from an illegal unit.I don't know Chicago laws, but in NYC if you have an illegal unit, the tenant occupying it seems to have more rights than the owner does and doesn't have to pay rent... 

With all my respect, most real estate agents have no clue what the laws are.

You've probably heard of big Landlords losing property, but only because they were flagrantly violating Fair Housing, running a slum, or otherwise egregiously violating the law.

It offers affordable housing, solid rental demand, and generally favorable landlord laws.

You need to think about not just the potential income but also the potential problems such as city ordinances, state law, insurance, potential eviction issues, etc.

There's nothing in the law that requires you to send someone on a Sunday evening at her convenience.

If there is one thing I would do different is: I would invest Out Of State in markets that had sustained growth, strong job numbers, were safe and desired, and had favorable Landlord laws.