@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.

Investors who are active in gathering data on local trends while working with knowledgeable agents are able to pick neighbourhoods poised for growth and also comprehend how to best mitigate their risks as they prepare to maximize their return.Myth 3: Distressed Properties Are in Bad LocationsAnother misconception is that distressed properties only exist in bad neighborhoods.

Happy to serve as a resource if you have any questions about the local market.

I would echo this, it is a great REIA and the best place to find local, like-minded individuals and resources. 

If you are willing to live in urban areas you may want to talk to a local bank in your market and see if they have any incentives or grant loans for certain areas.  

I'm a local real estate agent and would love to help you out on making this deal work.

You could get a loan from a local bank or private lender to fund it

Find and attend your local REI groups. 

Why don't you join a local landlord association?

Network with local investors to understand what formulas they're using.3.