I agree with Ali Boone that you need to have a good team or an active investor to partner with to ensure your investments achieving the desired output.

Position myself properly.

Possibly my worst is some wallpapered ceilings (tin pattern) that didn't adhere properly and started peeling long after painting.

Did they give proper notice before leaving?

One of the tenants has not paid April rent, and the landlord has given proper notices and just filed paperwork at the courthouse.

Or, is there some distant cousin that's going to show up with a valid claim that they had some ownership and were not properly compensated? 

As used herein, "preservation improvements" shall mean improvements made to preserve the property by properly keeping it in repair for its proper and reasonable use, having due regard for the kind and character of the property at the time of sale…My guess would be no, but I'm not sure.

Any recommendations for 1) brokers who could do the BPO (ideally I bring the broker to ensure Independence); and 2) an Illinois lawyer who will know the mechanics of setting this up?

But I am looking for someone who can help me properly set things up so I can reap tax savings now, and in the future. 

You're also going to have a hard time (in my desirable markets/locations) finding someone to A) sell you a house at a significant discount and B) not getting ripped off or properly est/budgeting your repairs.What's far more likely to happen is you buy a house from "wholesaler".