I appreciate everyones response and opinions. I feel like the question I posted is getting about a 50/50 response from everyone I ask, on this forum and elsewhere.
Seems like everyone agrees that getting on with a place like Frontier or Allegiant would be a far better move than with SkyWest or ExpressJet. Makes sense.
I still feel like the lack of jet time will prevent me from moving directly to a major, no matter how much hiring they will be doing in the next few years.
Also, the B1900 is nothing like a Q400 or a larger, more sophisticated T-Prop. The Q400 at least has glass cockpit and an FMS. The 1900 is similar to an EMB120, but most Brasilia captains are at Skywest and probably all of them have CRJ time, which I do not, making me less competitive than them...
What about the total time issue? Great Lakes is running really short upgrade times right now. We have guys upgrading in less than a year. That upgrade time is great at all, but it means you could get your 1000 TPIC and only havw 2500TT. Where most regional airline captains are not getting their PIC time until they have at least 3-4,000 hours. I personally have under 4000 TT.