So since I no longer had access my old cell phone number then I was locked out of baselane.On June 25th I attempted to contact support to have my cell number changed in their system. 

The facts that she was late twice and didn't even attempt to make a partial payment or talk to you says it all. 

The tone of his email implied he had been unable to reach my PM after "several attempts."

Yes the financial benefit is attempting, but I do want to understand all the legal consequences, including insurance issues before making a decision.

If the unit does not comply with local codes (like proper egress, zoning approvals, safety standards, etc), it cannot be legally rented regardless of how it’s marketed.The safest course of action forward, would be to bring the unit up to compliance with chicago's zoning/ building codes before attempting to rent or advertise it. 

I’m a bit of a nerd with an analytical streak, attempting to break out of my shell and be more social—so if you see me in real life, get ready for a nerd trying to be outgoing!

Attempting to collect from someone who has no incentive to pay will drastically lower your chances to actually get the agreed upon money. 

Neither I nor others have any idea what has happened to the money, and despite numerous attempts to reach out, there has been no response from him.

I recently attempted this with an FHA loan for a client, but it was unsuccessful.

Really no reason to attempt to do this with an LLC.