Are there any regionals that don't have good training these days? Don't they all give extra training if needed? If not they should unless the person doesn't have a prayer.
But when Air Wisconsin is paying $40k in bonuses over the first year and Endeavor is paying something similar, is Skywest really competitive?
I would be inclined to go where the biggest bonus is, even if the upgrade is longer. I expect there to be regionals hiring street captains or close to it pretty regularly the next few years. So one could take the 40k in bonuses (or more at some places) and in a couple of years take an even bigger bonus going somewhere else as a captain.