Obama's greatest flaw is his need to be seen as a post-partisan compromiser. In his quest to be liked, what has happened is that he's failed the people who got him elected. Sometimes middle-ground isn't the best place to be standing; especially when one side is running to the farthest corner, playing up absurd fallacies.
What's even more disturbing is that Obama had the votes to pass his health-care reform. But his attempt to make a public attempt to woo Republicans and engage “regular” Americans in town halls, has resulted in the failure of anything resembling health-care reform. He has caved to big Pharma, and it appears, has abandoned the public option, essentially just extending the status -quo in this country, but putting the insurance companies in enough tight spots to make it appear he's making a difference, and giving the right something to rally around.
Obama can give great speeches, but he can't seem to, for his political life, keep himself, or his administration, or the rest of his party on message, as the former administration did with their monolithic, but successful talking points. Bush couldn't pronounce Nuclear, but he was able to get his legislation passed.
This isn't only Obama's fault. It's the leadership in the democratic party. Rahm Emanuel, who worked the deal with the pharmaceutical industry, seems to be more of a political opportunist than a deal-making enforcer of a certain ideology as was Karl Rove. Nancy Pelosi can't seem to control her people in the House, and Harry Reid, who has the charisma and political power of a bookshelf, seems to have even more trouble in the senate. While the Right has a persecution complex, the Left has a devastating phobia of being rejected, and in-turn, fall into making self-fulfilling prophecies. By trying to get everyone to like them, they come across as so spineless and bland that they're still hated by the right, a necessary evil for the left, and tolerated most of the time by everone in-between.
The GOP made the mistake of being too acquiescent to their base, and ending up on the fringes. The Democrats have gone too far in the other direction, alienating their progressive base, and being stuck in no-man's-land. If the Democrats wish to succeed in any of their political goals, and not just remain in power until the GOP returns with new leadership and ideas, then they need to tap into the progressive base which got Obama elected. His failure to engage his grassroots support, and instead try to reach compromise, has wasted the great network he had in place after the election. And if he continues this pattern of compromising principle for the sake of reaching a compromise, that network, and that base, will find a different set of candidates in 2012.