I am DTW based and live in DTW. I'd say go Endeavor. PM me if you have specific questions and I'll be happy to chat.

Regarding upgrade time: one thing to keep in mind, more and more majors and basically all of the LCC's except Southwest are hiring with no turbine PIC time so you may not have to wait for an upgrade at a regional to get an interview at a (lets just call them) real airline. Spirit has a DTW base that goes quite junior and a quick upgrade. You could put in a couple years at Endeavor, go to Spirit and be a Bus captain by 2020 with a couple lucky breaks. Majors love to scalp pilots from their LCC competition so you could go from there to DAL, United, whatever.

If you are young and single, I would strongly consider an expat gig. Emirates, Quatar, Korean, there's others but it's not my cup of tea so I'm not that up on it. Suffice it to say you'll make enough in 10 years to retire.

Anyway, let me know if you have any questions about Endeavor.

Good luck!