Maybe some AI pro can provide a solution?  

So before I transfer ownership back and start a seasoning period, I thought I would ask if there were any solutions I am not finding.  

I can provide you with some CPA and lawyer references that support real estate investors.

Happy to help --What are you referring to when you say you specialize in this specific issue?  

The solution is to work it out, with the developer paying you more than the redemption price tag, but less than the legal fees it would incur to fight about it. 

I've heard people refer to Santa Ana winds with the Bay Area but I wouldn't think it goes this far up north. 

Quote from @Pavan Kumar: Quote from @Kyle Mccaw: @Pavan KumarWinter is indeed tougher for rentals, but taking your listing down isn’t the solution.

Here's the City link for you to reference. https://www.chicago.gov/city/en/depts/doh/provdrs/homeowners...1) ADU regulations specifically exclude Short-Term Rentals so don't do it if the intention is to short-term rental. 2) The ceiling height oh 6'10" is almost guaranteed to trigger digging a basement if you want to formalize as an ADU unit, especially if that height is further reduced by pipes or HVAC. 3)Ingress/egress is an issue for renting, as is that any bedroom also will need two (ie operable window/doorway).

Save related articles to the cloud for reference. 2. 

You could start with your agent or a local agent who supports investors and could have contacts to refer to you.Lastly, you could consider negotiating with a local PM to take on a hybrid approach to management.