I have a different impression: I believe that President Obama has little patience for political theater, a pretended devotion to maximalist positions that the advocate knows will never gain majority support, that it's possible to identify a consensus position that reasonably advances the public policy goals of even major legislative initiatives in a manner that is acceptable to both sides, and that it thus saves a lot of time and bother to bypass the theater, start with the consensus position and focus on the details.
I do believe Obama made mistakes in his pursuit of healthcare reform, most significantly in assuming that the Republican Party would participate in the debate in good faith, and that his own party would recognize that getting squarely behind healthcare reform would be best for both their party and the country. Instead he got "the Party of No" on one side, and a mad mixture of pandering and demands for pork from his own party that left a lot of people with the impression that they had learned nothing from the Clinton years and weren't fit to govern. The Democratic Congress had the option of demonstrating leadership, if for only a few months focusing on what's good for the country and how to make the best possible healthcare reform bill, and... largely chose self-interest. Had they followed Obama's lead, the difference between the initial framework he proposed and the final bill would have been minimal, but they would have appeared effective in office.
I get the same sense from Obama's tense interactions with Binyamin Netanyahu over restarting peace talks with the Palestinians. Obama appears to accept the consensus view of what a final resolution will look like - at least if it is to be a two-state solution. That is, there will be a final border that roughly follows the Green Line, the Palestinians will have a capital in East Jerusalem, and the end-result will be a genuine Palestinian state alongside Israel. Netanyahu lacks the personal courage to commit to such an outcome, and perhaps more to the point does not desire that outcome. In Netanyahu's initial term as Prime Minister, his government's contemptuous view of what a Palestinian state - a rump state with no control over its borders, water, or airspace, might look like was reportedly, "Well, they want to call it a state? Fine, they can call it fried chicken if they want to." It's obvious that peace can never be achieved on those terms, and it appears that Obama would prefer to work with grown-ups on both sides to start negotiations from the consensus view and focus on the details.
Today, a new criticism - that Obama is offering to allow offshore drilling in areas that were previously off-limits, in order to try to entice Republican support for climate legislation - as well as feckless Democrats like Mary "Louisiana Purchase" Landrieu. Without Republican support, the bill will die. To me it appears that President Obama is starting with the belief that offshore drilling will eventually happen, with the actual debate being over when and how, in a context where the concession will achieve a great good (getting the climate bill passed) based upon a relatively minor concession - and with significant oversight of environmental concerns. If it works, he gets his climate bill. If not, the bill dies and the offshore drilling proposals don't become law.
If my inference is correct, Obama's biggest mistake is his hope that people will rise to the occasion, recognize that maximalist positions will not work, and commence good faith negotiations based upon "what everybody knows" is likely to ultimately happen. For healthcare reform, it took a year for the legislation to evolve into a form remarkably similar to President Obama's proposed starting point. For Israel-Palestine, we have forty years of history that tell us that negotiations that start from maximalist positions will accomplish nothing. For climate legislation, if his proposal works he'll get a bill while making a concession that is very likely to occur in the future, but on his own terms - as opposed to losing the opportunity to pass climate legislation until after the midterm elections.
Update: From Obama's remarks,
Ultimately, we need to move beyond the tired debates between right and left, between business leaders and environmentalists, between those who would claim drilling is a cure all and those who would claim it has no place. Because this issue is just too important to allow our progress to languish while we fight the same old battles over and over again.To me that again sounds like, "We all know the approximate destination, so let's skip the theater and work out the details."