From what I've heard, you will never upgrade. The Dashes are oldies but goodies. Problem is, (no disrespect to the prop drivers) T-prop time is becoming less valuable as more and more RJs guys are out there. A lot of guys will say turbine time is turbine time, which is true on paper. But flying long legs across multiple weather systems and then coming down final at 150kts vs 90kts is a big difference, as is glass time, and hiring committees know this *ducks from the flaming fireballs coming from the prop guys*. As more and more heavy metal becomes glass, glass turbojet time starts looking better and better. The long and short of it is this: go to PDT if you have no other options (like you're one of those numbnuts who want to get hired at a regional at 19 or have been turned down pretty much everywhere else) or live in a PDT base and don't want to move and don't feel like you need to fast-track your career. Most people who go to PDT end up making the jump to a "better" regional in a year or two anyway. If you live in a PDT base then it could be ok for you (assuming you don't expect to upgrade in 18mos and then jump to FedEx a year after that) but there are better places to be.

PS.
An associates degree will let you do just that: associate with people who have bigger and better letters on their resume (like BA, BS, MBA, PhD, etc). It'll work for the regionals but unless you know some one high up on the inside at a major, you will need a 4 year degree. I've flown with several captains who can't seem to move on no matter how much help they get because they don't have a 4 year degree.