JamisJockey, I think their vacations, and especially Mrs. Obama's, are symptomatic of a larger problem the Obama's have, that being a complete disconnect with regular Americans. They've lived in an academic and intellectual bubble for their adult lives, one that's entirely different than what the average middle class American experiences.
They're very bright people, but they have no sense of public relations (or so it would seem). They're not in tune with us, so Michelle Obama probably didn't see how her "first time I'm proud of my country" remarks would be received by most people, nor can she see how people who are hurting look at her globe-trotting to exotic locales.
Clinton, Bush I & Bush II, and Reagan would all have realized that you don't take expensive and frequent highly visible vacations when 10% of the people are out of work. But Clinton, the two Bushes, and Reagan weren't ivy league elites.