He has a bit more experience but we both still have a ton to learn.We will be posting the "Notice to Enter" on our auction house tomorrow and are hoping the occupant (we believe it is the foreclosed on former owner) will just say "okay, I see it's my time to go." 

@Zantiago Zurita , if you are buying as owner occupant, apply for a 203K FHA construction loan.

No big deal, it's just a P&S contract you are assigning.Steer clear of occupant buyers, assign contracts, and you'll have fewer legal risks.

I have found a duplex for sale that was purchased from a bank in Oct of 2013 (I saw the listing when it was for sale thru the bank, but was not in a position to buy so I didn't look at the property), the current owner...

Some C areas of Chicago are still below 50% of the peak and, I would bet have much more room for equity growth, in addition to immediate high cash flow.If you are determined to house hack in order to qualify for owner-occupancy benefits, and I don't know the exact rules, but you may only have to "intend" to occupy for 1 year which is not that long, especially if you are focused on the rehab.  2 months in, your initial bona fide intention can change, and you could move out within the guidelines.  

Unless I had occupancy of 40% or more, I would not make more than renting it out traditionally.

What is the current occupancy of the property?

Landlordreserves the right to restore the landscaping to its initial condition, as itwas at the time of Tenant’s taking occupancy (possession) or at the time ofinitial restoration if performed during Tenant’s occupancy. 

Does anyone have any knowledge about "Property Damage Inspector/ Occupancy Inspector" jobs?  

Also you should run the property through the rental property calculator, if the property cash flows with full occupancy, (accoutning for vacancy and other expenses, that is a property worth considering) take your personal preferences into account as much or as little as you want.