Sounds like you've been thinking a lot about it, which is more than many people do.

With the possibility of your boss getting a Citation, this is beginning to sound like an airline/corporate crossroads decision to me. So, perhaps the first priority is to try to decide which you would rather do. If the choice is airlines, I am more of the school of thought to get on with a 121 carrier as soon as possible. While most everyone tends to think the regionals will still be hiring in 6 months, you never know in this business. Plus, if you do wait, choosing where the "good" place to be will not be any easier. The Cathay SO idea sounded interesting, definitely worth a look. Prioritize, explore, and make the leap. Best of luck.