But that is often an "apples to oranges" comparison unless you're going to live in the property/house hack.Got it.

For an estimate of this size, you absolutely need a second opinion on the necessity of the repairs and you also need comparison pricing. 

Your marriage success comparison to RE success comparison is false on many fronts (unless you literally treat marriage as a business transaction and nothing else, but even then the downside is scary).

I did a quick comparison for 2 bed room units, and found similar styles nearby going for $800-$850. 

900 sq ft I would think you can go 3 or 4 ton, dont see why it would be $6k that seems high.I had TWO units installed 2 years ago (5 ton 1st floor 2k sq ft and 2 ton for 2nd floor) and it was $6k total for both including install.for good comparison on the unit prices themselves http://acunitsdirect.com/ remember as with anything an installer will mark up those prices thats why you get higher quotes

Sounds about accurate.What you should be focusing on is hopefully you are getting a return(Cash-flow) from your rentals and you are not paying tax on that.This would be better in comparison, to other investments such as dividend or interest income.

In comparison to the FHA 203k Loan, the homestyle loan appears to be a better fit for me.

Will also consider composite and granite depending on cost comparison.

If you're working with a tax pro, they should be able to run a comparison for you to show the differences.

Chicago is still pretty cheap in comparison.