If you trust your friend then the benefits will likely outweigh the risks.

This indicates two things:The company's perceived the Chicago and Illinois fiscal risk to be outweighed by the costs or relative disadvantages of moving to a city that did not necessarily posses the positive characteristics that Chicago does.I would also suspect (as you stated) that these companies received a sweet tax incentive deal to move to the city, however I do not think a city the size of the Chicago would provide tax incentives to companies to move there that would not eventually benefit the city/state in the long run.

The money I make here outweighs tax advantages of other states.

The advantage with those was that I could have closed in my LLC name......but the benefit of the 30 yr amortization coupled with the fixed rate outweighed that enough for me to deal with the mounds of paperwork and putting property back in my name for refi. 

But now it seems more clear that any benefit of lower pricing from a GC partner will be outweighed by giving the contractor a piece of your deal.

The one positive so far is I literally build it how I want it, I am just not sure if that's enough to outweigh the time it actually takes to do it.

I am facing the dilemma in the fact that I wonder if starting now outweighs my patience and coming in to swoop up multiple properties when the time is right.

I believe you mentioned that you also purchased that place at or around 600K, did that price make sense w/ the current NOI that the sellers were collecting or were you and your partner purchasing it knowing that the future NOI outweighed the fact that the current numbers weren't good?  

Does it outweigh all the hassle?  

Markets vary but strategy and the will to succeed outweigh the differences.