DR Matthew -
Regarding your potential move to Chicago... What kind of a support network do you have in place (do you already know people there? do you have leads on work once you get there?) Also, have you investigated housing options (how close to downtown can you get for your budget, etc.? Also, don't forget to factor in a major budget factor: how much it will cost to transport your stuff. Not trying to be negative, just practical, having just gone through a major move myself.