I'm based and live in DTW as well. As BATOL said I think Endeavor is your best bet man.
With the current hiring and worst case scenario attrition from the top (a contractual number that must go to Delta) you're looking at 3 years max for upgrade at Endeavor but you'll make $60k extra during those 3 years. Say you upgrade in 24 months at some other regional. Sure you make more as a captain but do the math... what's the total earnings over say 5 years?
There's also the living in base factor. Reserve is an absolute cake walk if you live in base. I've been on reserve several days this month and haven't touched an aircraft since April 1. Can you imagine sitting in a crashpad at ORD during all that time? I've been at home in my sweats working on stuff around my house and hanging out with my dog and fiance. Good luck doing that in a crashpad.
You could just move to a base at the quick upgrade airline I suppose. Good luck paying for that though on their pay.
There's many paths to take but the music almost always stops for awhile. Where do you wanna be when the music stops?
PM me if you have any questions about Endeavor. Go Broncos!