I think finishing school should be your top priority. Get that BA out of the way. I think a lot of people that go to the regionals lose sight of that. And then when the majors start hiring again, they have the hours but not the degree. And I imagine it is a lot more difficult to get the time, money, and motivation to get a degree when you are Captain at a regional.
Also, HR people don't really like "lateral" moves in jobs. But I don't think moving to Skywest is a lateral move. HR departments do favor 121 time, obviously, because that is what they run. But your check airman experience is a definite bonus.
I am not sure how quick the upgrade is at Skywest, but with your hours you could go somewhere and upgrade pretty quick if you wanted to. Then your building 121 Captain turbine PIC time, which is one of the most valuable times that the majors look at. It doesn't matter if your flying a B1900 or a CRJ. It's 121 turbine PIC.
But with your finances, it would be tough to do the move right now, and I wouldn't work extra jobs to try to do it.
My vote is stay, for now... and most importantly get that degree. Then if you think you can get a decent 121 job somewhere, and you can afford it, go for it. But don't go somewhere where you won't upgrade until 5 years (American Eagle). With your experience, an FO job at a regional should be fairly easy to get, so don't think that just because your in the Skywest pool you should take the job.
Good luck to you!