@Jimmy Chou I appreciate the response.... yes I have seen that we're looking in a very popular area, if it was just me I'd live anywhere that I could find a deal but that's probably not realistic with the future wife. Although she is more than willing to get into a project property as we've done full renovations in the past together.
We really don't have a great system right now for the rentals though I know I need it, seems the hardest part of that for me is the work order mechanism.... right now my go to guys barely operate a cell phone let alone a computer or technology that could help me out.
The other piece to the puzzle is that if we don't sell one or several of the properties, buying a place in chicago is probably not realistic right now as I just don't have the cash for the price ranges of Chicago properties compared to here. So we're in the debate right now on whether to rent for a year or try and do a short term rental and then buy as soon as find something.