In the current situation Obama is doing it right and you have laid out why. I still believe that from Day One in office he started down a road which would inevitably bring on the problem he now faces. What his opponents saw was that he preferred being understanding and expecting the rest of America was going to be happy about it.
Healthcare was an unpopular issue and when the poor guy was saddled with the economic meltdown, I think he felt he could and should do it all right away. He was going to be in trouble on the economy no matter what but it still required a full frontal effort. He felt he had to get into Healthcare right away and his advisors told him that was the way to go. The result was less than the economy needed and he was getting the blame. His healthcare efforts began "in the middle" by giving up on a majority of it and negotiating the rest giving up more and more until the final result was close to nothing at all. Why he did this I don't know. Small balls? Bad advice?
The best thing he has going now is the Republican yahoos in Congress and the ones who are running for the Presidency. Romney has just put out an ad that tries to show Obama has shifted from "his own words." The fact is they are not his own words and the last guy to call someone else out like that should be Romney who has expressed 5 opinions on every issue.
Obama's current set of advisors are doing a far better job than the first batch. With a stronger group of Repubs I would be worried a lot more than I am. "We've refused to quit." I like that. In it is the room to control a negotiation and still hold your ground.