Thanks for all your help...
I am currently waitlisted on the outbound, and got an upgrade on the return via Boston. Lucky for me, because I actually live in Boston, but need to go back to SFO for work. So during my stopover in Boston I can go home for a fresh set of clothes!
Is there a difference between being on the priority upgrade waiting list and a normal upgrade waiting list? Sometimes, the agent on the phone would say that I have put you on the priority waitlist, but does that really mean anything?