The #1 reason I would have never voted for him was his healthcare plan. People bucked at the idea, AT LEAST half the country didn't want it. So he let his plan go get cannibalized and fucked to the point where it benefitted nobody, people STILL balked at it and he bulldozed it on through anyhow.
The one thing I wanted to see him do was get tough on lobbyists. That was little more than campaign rhetoric.
Cash for clunkers was a joke and a band aid. The auto bailout was a horrible idea (and in all fairness was a ball Bush got rolling). GM needed to declare real bankruptcy to get out from underneath all of their debt, lopsided contracts and backbreaking deals with the UAW. But since he's a slave to the unions Obama propped up GM and put them on life support to pacify the UAW.
The financial instutions bail out is neither here nor there. I wasn't for it, some say it was needed, I'm not a psychic, so this is a push.
Then there's all of the bailout money that's gone out and is largely unspent and will be used as political favors for those who's jobs are on the line. That's politics, still think it's shitty and money we didn't have to give out though.