Has anyone had any experience that they can share concerning Real Property Management Suburban Chicago?

I would be concerned that he has other liens on the property, I would check with your foreclosures laws in the area, in Md. you could get in trouble dealing with someone with pending FC,I dont think he is in a great position to be negotiating.

I will admit though that I am 6'2 and quite the big guy, as well as usually carry some kind of weapon (I never leave home without a pocket knife and carry an asp if I'm concerned). you should be fine as long as you limit their access to your house to the garage, vet them over the phone, and have another person with you at the time of transaction.

So, I personally don't think you should be concerned investing in a cold climate. 

A 10 oz soda spill made on a wood or tile floor is a simple wipe up but permanent damage to carpet and pad.  

Is this reason for concern, because at this point we are concerned.

My only concern is the insurance stating "no dogs".

One mistake I made was I put too much time and made my bid pricey, after a few great comments, and giving out favors in exchange for feedback, we have adjusted to an "investor mindset" and have been hitting the sweet spot where it brings everyone to the same plate.Lessons I learned during this learning curve was, not all want "retail" quality finishes (where all our commercial and government contracts are of the only concern), they are more concerned about time and money.

@Steven Picker, your foreclosure and underwriting concerns are valid, but that's going to vary hugely from state to state.

@Steve EllisonWell, for better answers about your tax concerns, need to speak with a CPA.