Putting an offer in is easy, it doesn't require all of the contracts etc, your broker just fills in a 1 page form and if it's accepted they email everything out.

Do you happen to have some sort of cheat sheet of a list of neighborhoods in Chicago and what class they are considered to be in? I

Anthony's suggestion of continuing to pay your regular rate of rent once you move in is a good one. 

We've got the management software and maintenance requests set up to proceed with self-managing but getting a new tenant in is challenging and time consuming to plan around with our our W2 jobs. 

Or military moving in?  I

I currently have two properties, one i rent out and the other I live in (I plan on renting it out).

I found that once I moved out of the market I lived in, I could pick the market that was best for the numbers I wanted.

If you decide to dig in, I believe you will get very excited about what is happening now.https://www.biggerpockets.com/forums/888/topics/849570-nesara-gesara-financial-reset-greatness-incoming

I let tenants know up front they need to make arrangements to have them in their name and that I have already arranged the disconnect on move in.  I

Perhaps renters nit pick a little more when they first move in?   I