http://michaelochurch.wordpress.com/2012/12/12/fundamental-s...
TL;DR: People have to seem more open to subordinate roles than they actually are in order to get jobs.
It's not always greener on the software side of the fence, though. Much of the job is dealing with bad legacy code, which seems to hurt you more if you're a good designer (cf. first and second design paradox) which your well above-average writing skills suggest you are.
I like Chicago a lot and think that it's a great place to live. Honestly, I think the obscene cost of living in New York and San Francisco has a negative overall impact on the quality of businesses that can be founded, but that's a rant for another time.
Good luck!