If Obama had taken on the health insurers, Republicans would have had a harder time assailing the Administration over "Obamacare," and particularly at the charges that health care reform will raise rates.
On the other hand, we might not have health care reform or financial reform on the books, even in their highly imperfect forms.
One thing is, however clear: The President should have been much stronger at criticizing Republican obstructionism from the beginning, and he should have made it clear that the bills he signed had many flaws and were only first steps toward real reform. The political people in the White House should have resisted the understandable, nay, inevitable, urge to celebrate the passage of health care and financial reform and urged the President to make the signing ceremonies muted affairs at which he noted the progress that had been made, but coupled that with strong statements that we need to go much further--with specific statements of the direction that further change should take.
Oh, and Mr. Obama should not have surrounded himself with people who were in the Wall Street club. He didn't do that on health care, and so you don't see Republicans attacking the administration for being too cozy with the health care establishment.