The firms focus is in commercial property and I have learned an incredible amount about navigating city and county regulations, dealing with complicated leases, permit running and expediting and so much more.

Either way, you can't go wrong with him if that is your intent.However -- I'm a bit confused why you're jumping directly to his firm, and seem to believe he's the only one in the country that can add value.  

Around me it is normally the law firms that handle the sales that publish the list, so you may have to make a few calls, find the right person, find the right legal publication, etc to get to the right person who knows what you're talking about.   

His firm is staffed to handle transactions all throughout the Chicago and the surrounding burbs.

@Darren Phane In my opinion I would say dive-in for 6 months to a year working independently within a firm that is supporting you!

One google large pm firms in your area of interest. 

Get a license, join a RE firm with access to an MLS for your area.On bigger multi-units, call CoStar, I'm sure for $400-$500 a month they can help you out :)

@Joseph Davis Britt Law Firm on 720 N 3rd.

Firm handshake. 

Only 3 firms (Shopify, Twitter and Square) have announced permanent WFH.