How did Vilsack, a Governor of Iowa, manage to lose Iowa?
Obama obviously has more charisma that Vilsack, and also had a lot more cash than Vilsack had. Vilsack didn't win any debates or come close, and didn't have the endorsements that Obama had. If Iowa had voted on Super Tuesday, Vilsack would have won, as Obama or Clinton wouldn't have spent nearly as much time or money there.
He still was a relatively popular governor of the state, and cash doesn't really matter in Iowa (Romney vs. Huckabee, for example), personal appeal does.
I'll be quiet now, though, please continue.