Their property sat vacant for a few months while their guy "saved them money".

I'd recommend listening to this episode of BiggerPockets Money and then using the linked spreadsheet to help you decide https://www.biggerpockets.com/blog/money-572

Hope is a bad strategy.The only on market strategy that I think can work is paying cash/line of credit/hard money for a property that does not qualify for conventional financing.

I've done and been a part of many Chicago zoning changes...they take a very long time and a lot of upfront money...unless you are planning to add multiple units and do a full renovation, the ROI is probably not there.

It’s obviously not money.  

Thats a lot of work that a company would have to do and they would want their money back on the development costs.

.: You will also owe depreciation recapture tax. 

I am the boots on the ground and provide all of the time and my partners supply the money.

All that being said - follow the money. 

Let us know how it goes.I provide my screening criteria on my website, and I encourage applicants to screen themselves before applying so they don't waste my time, their time, or their money.