Generally, no nightmares, because I told all potential tenants right up front, “I am calling your prior landlords, I will not accept any evictions or criminal background more than the occasional speeding ticket”.

Once you've got a shortlist of 1-2 providers, schedule visits - the couple hundred bucks you spend on the flight will be the best investment you ever make.

Even though they are relatively modern homes, having a better cushion would prevent you from dipping into your cash-flow for any big ticket items in the future.

We're going to be passing on this property since as many of you mentioned, this may be a one way ticket to some serious pain.

(cheap flights when something goes wrong...?) 

There is a flight to safety, which combined with higher cap rates in the major markets, leads many of the larger players to retreat back to the big cities - if they are not on the sidelines altogether.  

Then again, considering more than half the trustee sales get postponed for one reason or another, might not be worth the flight.

Plus most guests are up and out the door before 10 anyways if they have to make a long drive home or catch a flight..

I'd also look at a 'flight to quality' and stay away from the 60's and 70's assets that will have the inevitable deferred maintenance and system replacements coming due, especially plumbing.

You can definitely find some condos for $120-140k in some areas of Chicago and surrounding suburbs and you could also utilize a renovation loan to maybe handle some of the bigger ticket items like kitchen and bath, then maybe paint yourself.The other option is just to continue to network, build your team, and educate.