Thanks to everyone, the information and advice has been very helpful and I have follow up conversations scheduled with Expressjet, PSA, and Envoy.

One question I still have, is what does it really mean to be the last guy in class who gets assigned as an FO to the 145 at ORD? (that seems to be where the last picks go) How long is reserve, do reserve pilots get any flying time, is it worth bidding out of ORD if that just lenghtens your time on reserve? How much does it cost to live in ORD? Basically, other than everyone saying "it sucks", what does it actually mean, day to day?