Do you believe that the outcome to date would have been better had he acted more forcefully with respect to (say) the health care legislation?
I'm not Bi-Polar Bear by I do believe that, yes. Legislation is a bargaining process; Obama entered the bargaining process over healthcare with a lukewarm compromise position, and signaled from the beginning that he wasn't intending to put up much of a fight over it. So it's little wonder that at the end of the bargaining, healthcare reform will be a diluted mush that isn't worth writing home about.
In my opinion, Obama could have achieved a much better end result by doing two things: i) open the haggling with with a tougher position such as Kennedy's Medicare for All or at least Edward's campaign plan, and ii) signaling an intent to kick some asses over it.
If confronted in such a way, Congress Republicans would have opposed that no more than they currently do -- after all, they're maxing out their capacity for opposition right now. Moreover, Lieberman, Tupac, and other Democrats positioning themselves as centrists, would just as happily "compromise" on a more aggressive reform plan. Their current opposition is not driven by any policy principle I can recognize -- it's all about positioning themselves halfway between what the president suggests and the Republican opposition.
Obama could have definitely gotten a better outcome by showing a little more audacity. Instead, all that healthcare reform leaves us with is timidity of hope.
I believe you are overlooking the (presumably) deliberately vague rhetoric that candidate Obama used so consistently during the campaign concerning this issue. He never unequivocably endorsed a public option as it is termed now. Indeed, on several occasions when asked, he evaded endorsing such an outcome. Instead he repeated his assurances that everyone should have access to health care (whatever that means) and that everyone should have the same quality care he (then) enjoyed as a Senator; and other things like that.
In office he handed the ball to the Democrat Leadership in the Congress (presumably wishing to avoid the Clinton outcome of 1993) , and continued to refer vaguely in his speeches, to the several variants being discussed and negotiated as "my plan". He has also repeatedly assured questioners that he is directly involved in the process, and to a degree that appears to be the fact.
With this evidence in mind I conclude that he wanted significant health care legislation and greater involvement by government, but wasn't particularly wedded to any particular solution. Perhaps this comes from mere ineptitude, or, alternatively, from the belief that the first legislation will merely be the foot in the door and that specific goals can be pursued later.
It also appears likely that from a fairly early point in the process the Administration focused on co opting various organized groups that opposed previous reform legislation. These include big pharma; AARP; the AMA; medical diagnostic equipment makers and others - each of whom got significant financial relief or direct benefits in all versions of the proposed legislation.
In short I strongly suspect that Obama will likely achieve the objectives he sought in this endeavor. It merely happens that in important respects they do not include some of the objectives of his enthusiastic supporters, who read whatever they wished into his calculated rhetorical vagueries.