I don't know for sure about Eagle but I am over at ExpressJet.
Upgrade Times: Upgrade times seem to be running at around 3 years right now at XJT. People outside the company seem really worried about the 69 aircraft thing but the general feeling inside the company is very positive. And I haven't come across that many Kool-Aid drinkers. Seems like every captain I flew with either just upgraded or has an interview/is leaving for SWA, CAL, Fed Ex, etc. I know right now they are upgrading captains as fast as they possibly can. Only time will tell what the 69-aircraft deal will do to upgrades. Thing you got to remember with that is that we will still be flying 205 airplanes for CAL. Latest rumors I have heard is that we have found work for all but 15 of the aircraft. So really, I think the impact will be negligible.
Benefits: We have one of the best 401k packages. We get an automatic 5% contribution from the company plus a 100% match up to another 4% of your pay. That number increases the longer you are with the company up to 6% i think. Pay and workrules are some of the best out there. Block or better, trip protection, 100% pay for dead heads, etc, etc. There are a lot of discounts and travel deals we get through CAL as well (I mentioned I worked at Continental Express and I didn't have to pay the app fee or the deposit at my apartment).
Training: Training is very good. Brand new training center with our own brand new, custom built, in-house sims (3 of em) and fully functional FTDs (2). No paper tigers except back at the hotel for practice. I have flown both the XJT sims and the FlightSafety ERJ sims and ours are about 10 times more accurate. You will either do your sim training at the training center at IAH or they will send you down to Houston-Hobby to do your sim training at FlightSafety. Its just luck of the draw. Training is roughly 8 weeks long and all of your hotel stay is paid for. In addition, you also recieve a per diem check for about $1500 during the first week of training.
Hope this answers some of your questions. If you want to know more, feel free to ask.