I actually have a webinar i put on a couple of years ago walking through all the pitfalls and mistakes I made doing 482 BRRRs between 2009-2018 in Chicago. 

Hi @Abigail King - Love that you are coming up to Chicago for some meetups. 

The Chicago Association of Realtors'® specifically state "When you become a Dual Agent, you owe equal fiduciary duties at that point to both parties in the transaction, and you lose the ability to negotiate for, strategize and advise either one."

I'm currently planning to purchase a commercial multifamily building in Chicago with the proceeds of a 1031 exchange.

HUD does a non interest bearing 2nd that you might want to consider doing.

Does anyone have experience with this (even better if in Chicago)?

We have a Chicago general contracting business, and handling the field operations is a ridiculously heavy lift.As far as finding customers I think you'll have some good success with gorillia marking at some of the local investor meetups. 

For sure you need a lender who understands them VERY well - try connecting with @Jose Valdovinos who is here in Chicago, but lends across the country!

Just curious on possible strategies or suggestions from anybody currently thats an agent in the Central Illinois or Chicago area.

Welcome @Reno Philip,Great idea to start slower and get your bearings before jumping all in.