I think Taker will retain, and he might keep it all the way through to WM. Not sure about the Orton/Sheamus one, I'd probably go for Sheamus to keep it.
As for the winner of the Rumble, I'm gonna go for Michaels. Vince told him to make the match happen himself, so he'll have to win the Rumble to do that. It'll be him and HHH as the last two.