Check out the CRREIA group which meets in Clifton Park for meetups.

In addition to those above-referenced issues related to conversions, the additional unit(s) would require a parking space and enough lot area/gross floor area to meet the requirements in 9-703. 

Parking will likely be your biggest hurdle.

It's thorough, easy to use and easy to modify so you can include your own special terms such as quiet hours, how trash service will be handled, parking, and anything else that is specific to your property. 

There is also parking per unit and impervious cover that could be an issue.

Could put cargo containers and parking.  

A couple other neighborhoods I like besides the two you mentioned are Washington Park, Hyde Park, Woodlawn, and South Shore.I think that area will continue to be gentrified because you have the lakefront as well as CTA trains.Is there any reason you are targeting Chicago instead ofdoubling down in Kansas City?

What about drive approaches, parking lots, site lights, landscape, irrigation, etc.? 

Multifamily doesn't need any more pressure/demand since cap rates can really get low when too many people pile in, but I have to say that commercial real estate (including large MF) and other types of passive investing (mobile home parks, storage, etc.) can really make like much easier.

This is what wealthy out of country (many Chinese) who already made lots of money elsewhere do- they like to park their money in class A or B condos.