@Bracken Bjorn The answer is in the local data...and the data might look differently to you than someone else...it's really about your goals, tolerance for risk, available resources, and personal preference...

I've been hearing 'horror' stories of business (even large ones) ditching the Austin area...and Elon taking back is application to be part of Austin proper.  

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.

If the lease is ending be sure you have given the proper notice of non-renewal of the lease.

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. 

A handy search bar in the upper right makes it easy to find previous discussions, blogs, podcasts, and other resources.

These are the options I'm currently exploring:Do the proper notice on the 3 month to month units and stagger the increases, starting asap, so I only risk losing one tenant at a time.

@Dave Foster is a great resource for everything 1031 exchange.

It will easily be your most trusted resource with your specific case.2) Fema will not cover anything business-related I was told multiple times.  

@Jared Appel welcome and any resource you need this group is here to help!