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.

They may not be the cheapest, but he goes the extra mile to cover my butt when I am doing rehabs, etc..

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. 

I typically charge half once we are half way done with project and final payment once client is completely satisfied with work. 

They take 1 to 1.5 hours to sign and about half hour to prepare.

If you want to get into wholesaling, your money is gonna be made from advertising and half of that is from following up with people who deny you.