Since I have done both of these things wrong and right in my past, I can tell you keeping the client happy to a certain extent is a lot more cheaperWe have found that setting the proper expectations right up front of what we will and will not do seems to help solve going down this never ending rabbit trail sometimes.

     Firstly, this post is for anyone and everyone who hasn't had the opportunity to properly introduce themselves in the BP community.

If the unit does not comply with local codes (like proper egress, zoning approvals, safety standards, etc), it cannot be legally rented regardless of how it’s marketed.The safest course of action forward, would be to bring the unit up to compliance with chicago's zoning/ building codes before attempting to rent or advertise it. 

Seeing as how I'm not sure if you are communicating this properly, but one could be crossing ethical / legal boundaries --- maybe.Personally, the rental activity for that sort of property and tenant would not be worth the time.Thanks for letting us know. 

For many, the hassle isn't worth it, but with a properly written lease, an MTR operator can have sub-leasing rights that allow for MTR arbitrage.

Fix it properly, then rent it out to a highly qualified applicant. 

Maintain proper records, such as contracts, settlement statements, and promissory notes.4.

Other ideas that have captured my attention are finding a 4 bed/1.5 bath house that has room to add a stand up shower to make it a proper 4/2. 

Make sure your LLC is set up properly, and consider hard money lenders for more flexible options.

Sure there is a very small chance that something will go wrong, but with the tightening rental laws spending a little on a proper lease is smart.