Those two sites will literally cut your costs in Half. $600 

I've looked at many houses and made offers on a half dozen.

They have agreed to pay half the rent the first 2 months and pay an additional 50$ / month for the other 10 months to make up for my lose.  

About half of the units are tired looking and needs a little TLC.

The HVAC, which is your typical condensor outside and furnace inside the closet are about half way through there useful life.

I don't know if I can answer them all but I do have something to add.I assume you are going to live in one half for a while at least before moving on and keeping both halfs as rentals.Consider the location and what type of resident will be renting from you, and being your neighbor.  

Obviously with me being half way across the world I would hire a property management company.

This is going to be your easiest and fastest solution.

I feel like half my time in PhD school was devoted to stalking the real estate in Chicago and reading blogs on real estate investing :). 

I had a guy quote me approx $2700 for the work to remove the mortar and tuckpoint the stairs and chimney, and another contractor quote me almost half of that at $1400 for a complete rebuild (all new) of the steps and tuckpoint of the chimney.