My best advice is understand zoning and density to make proper land valuation, then proper DD.

It's a great starter book for the financial foundations of real estate investing: https://store.biggerpockets.com/products/set-for-life-revise...I would also recommend Small and Mighty by Chad Carson: https://store.biggerpockets.com/products/small-and-mighty-re...Real Estate Rookie: https://store.biggerpockets.com/products/real-estate-rookieHouse Hacking: https://store.biggerpockets.com/products/the-house-hacking-s...

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.

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.

Great tools that get updated regularly.I am on the lending side of things and would be happy to hop on a call with you anytime to discuss financial strategies and help answer any questions you may have about nearly any loan product available to help you on your journey, even if they are not products my capital partners offer.We are all here to help you learn and grow.

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

Quote from @Garrett Brown: Hey Kyle, you are taking the proper steps by switching in the long run.

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.

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.