Gordon,As a fellow new investor, I can relate to how things seem daunting when you are diving into the real estate investing landscape.  

The only thing propping the area up is continued southern expansion.

Incredible yet inexpensive landscaping is gonna be needed on this one, but it will work.

We paid market value and did some minor work (diy kitchen reno, converted bedroom to formal dining, new flooring in partially finished basement, landscaping). 1 year later we split up and I still reside in the house.

I would keep the reserves and use leveraging to invest for further expansion of portfolio

You should have put some landscaping in the front to give it some curb appeal. 

Of course I will collect what I can to use it as part of my expansion, but I do not depend on it paying me in the future.I plan on retiring, well working for myself is probably a better way to put it, in luxury and style.

Does anyone have a suggestion for a good landscaper in Chicago? 

You touched on some of the great aspects of this generously endless expanse of knowledge.

Kristine Marie Poe ....15 years ago was a fundamentally different landscape than today.