@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

Everyone's kind of saying the same thing here so that's encouraging! 

@Jared FisherRecommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

The tips on finding deals, analyzing properties, and studying the market are invaluable, and I'll start practicing the "four square" method as you recommended.Thank you for the encouragement to jump in and get started.

Being encouraged to communicate off platform/misspelled words are red flags.

I would encourage a deck as well. 

This will serve as proof of notice sent.I encourage you to do this today. 

We do encourage doing your own due diligence even though we are providing all this info.

I would encourage you to learn the market you plan to invest in now and to continue to learn about the different methods of investing.

If you’re unfamiliar with any of them I’d encourage you to do some research.