It's a site totally unwilling to hear any criticism of Obama, especially that which compares Obama to Bush in a way that suggests they may not be so different, and that's why it's valuable that you made the effort to have a real conversation.

He's wasting his time over there. I'll note for the umpteenth time on this site that dkos is not a forum for free flow discussion of liberal ideas - it is a forum to get Democrats elected to office in the US and keep them there. The site was cultivated with this in mind from the beginning, and the user base behaves accordingly. Given the kill or be killed environment of electoral politics in the US, there is no room for introspection of any sort. Stop trying to make that site into something it isn't.

you are the media you consume.

Long ago, as time is measured in politics today, I did a diary called "The Quiet Coup", which looked back to the Ford administration and traced the emergence of parallel power structures that, taken together, helped illustrate the capture of government by a power structure largely external to the traditional narrative of administration as actor, political field as the space of play. The Dick and Don show was a big part of it.
I was right.
Obama is not even a major player. He discovered this, I think, shortly after he took office, probably the first time he tried to walk over the line of permissible behavior and got slapped down by the real players. Who are the "real players"? My God, everyone from Glenn Greenwald to Naomi Kline has published everything but their DNA profiles.
Frank has detailed a fair selection of the areas in which his stated beliefs and objectives, pre-election, and the policies (or lack thereof) that emerged from his administration clash horribly.  
However,I disagree with the entire premise that it is useful to ask what Obama would wish to do, or what his administration could do, had he "taken charge". He's just not in charge, and never has been.
I believe him. I believe that his campaign rhetoric represented his point of view fairly if somewhat vaguely, and described  a position of general principle.
The problem is the size of the space in which Obama is allowed to play. It's pretty small.

Think back to the days of Ronald Reagan for a minute.
We talk today about the disaster wreaked upon the competence of government by the Reagan administration when they discovered they could not just discard social security and the rest of the commie entitlements so hated by the elite since the new deal. When they were unable to survive contact with the "third rail", they just staffed the agencies they wished to destroy with moles, embedded nitwits or saboteurs, and rendered them so incompetent that it was easy to make a case for the thesis that whatever the government touched turned to shit. Deja vue.
Yet it was a standing joke that the big Ron couldn't stay awake through a national security briefing.
So did this highly sucessful plan to sabotage government actually emerge from his alzeheimers' addled wit? Bah.
In fairness, I think old Ron actually snuck a couple through, but he was as much of a corporate shill as Obama has, of needs, become.

In the main, Ron agreed with his handlers.
Obama does not.
 Sadly, he searches for issues and policy areas that he will be allowed to move--and fails to shoot low enough.
Just tick off in your mind the number of times he has been ignored, countermanded, evaded, bypassed. Now, with DADT, after actually publicly announcing a policy change supported by a strong majority of the military officer corps, Admiral McMullen followed by a host of lesser chicken-salad-toting military asskissers just told the pres to buzz off.
A while ago, I also said it was time for Obama to take a gamble- to stake out some turf that he could and would defend, to draw some fire on a battlefield of his own choosing. He did not. He squandered the biggest pile of political capital ever amassed by any president in my lifetime. That is at least partly a result of his inability to confront, as has been pointed out, but-- his leash is too short, even if he would do so. And it's too late, anyway.

 

Capitalism searches out the darkest corners of human potential, and mainlines them.