1) Health Care Reform was a campaign topic. Hillary not going after it would have hurt her. It's hard to say what would have hurt more her not going after it, or Obama's drawn out attempt to get the GOP to compromise.
2) You can't assume that Hillary would have had the popularity needed to leverage in Massachusetts. Ted Kennedy dead and no action on HCR? It could be seen as betrayal.
Political dynamics are tough, and I'm not so foolish to think that magic bullets exist or that people can be them. I knew in 2008 that Obama would struggle. That's simply the name of the game. Remember, the GOP didn't come to compromise or get along; they came to disrupt and obstruct.