So, you sort of bashed yourself.Your situation sounds like a quality control problem. 

As long as you take down the deal you win either way and the buyer has some control to what suits their needs and risk tolerance. 

Shareholders have rights with publicly traded companies and they can control the value of the company as well. 

Not because of the fees, but because of the risks of exposing my investment and property to the decisions of others and a greater number of situations outside of my control.

Crime has unfortunately gotten out of control  in select areas but the Chicagoland area in general has seen a loss of people wanting to live there.  

Some areas are OK, other areas are still very very rough.Rent control is something to be very aware of.

This might give you a clue as to what you are looking at.If you got it off the internet, this could be anything posted by anyone, including properties that they may or may not control and are trying to either sell or connect sellers and buyers together for a fee.

I work 20 hours a week and have thus far been exposed to re-zoning,site plan control, landlording, managing and getting bids from contractors, valuation and a myriad of other miscellaneous tasks.I got this job by taking your advice and reaching out to local Developers, I sent cold (personalized) emails to 15 companies and ended up going to lunch with my current boss and hitting it off.

I contacted a few carriers but they will not extend coverage to management services controlling their owned properties.

You need to know all this well before completing a purchase.The operating budget will obviously tell you what they are spending money on for the current period, on things like landscaping, various routine repairs, pest control, pool service, utilities, and preventative maintenance.