This sounds like a nice idea, but I honestly have no idea how to help. So I have to make a joke:
Chat up the hot girl in the MLL and upgrade her once you find out she's on your flight--bonus points if she ends up sitting next to you
FWIW, 1) depends on the staff, GA, etc., and won't actually be clear until T-1 depending on the flight, since misconnects could still affect J loads. 2) is just a function of the people you try to upgrade.