In a year where Democrats are highly favored to win the Presidency and increase their Congressional majorities enough to turn Joe Lieberman into the junior Senator of the Connecticut for Lieberman party, it's a very, very bad thing that Obama is consistently ahead of John McCain in virtually every poll, and has been for months.
The central problem with the expectations game that the media plays was never that expectations were being set and then not being met by the relevant actors. It's that most of the expectations are set by people purposefully acting like morons. This post from January at Swampland (oh, Swampland...) is a quintessential version of the "expectations game" - Obama crushed South Carolina, proceeded to win the majority of Super Tuesday states, proceeded to win twelve primaries in a row...and that exact post, minus Edwards and plus other states, was the exact same "expectations game" Obama had to face for the next three months.
It kind of reminds me of the end of Wargames, where WOPR plays tic-tac-toe until it realizes that there are no winners. Except imagine if they'd forgotten to program in the ultimate goal of tic-tac-toe, so WOPR just kept playing until it decided what the rules where, declared victory, and then carried on with launching the entire U.S. nuclear arsenal into the Soviet Union's rancid Godless piehole.