One additional thought on expectations: Part of the danger in setting expectations too low is that at the end of the day, moral victory is no substitute for real victory.
I've read a lot of stories reporting that Hillary Clinton's campaign is trying to set expectations that Barack Obama will win every single primary and caucus in the month of February (some 10 contests in all).
I know that this theoretically makes it look like a big win if Clinton manages to go, say, 1 for 10 or 2 for 10, but there is a limit to pursuing the strategy of relative versus absolute expectations.
If you're trying to win, predicting that you're going to lose seems to be a rather dangerous tactic--just ask Rudy Giuliani.
If I were Maggie Williams, Senator Clinton's new campaign manager, I'd have my people focus less on why they didn't win previous elections, and more on why people should vote for Hillary in future ones.