Nick Confessore over at TAPPED writes:
To put it crudely, Obama is the black candidate African-American voters and middle-class whites both feel good about.
And it’s too true. From what I could garner when I was back home, the view of Obama in middle-class white Illinois is that he’s like the black orphan that the nice white family adopted and oh how generous they are and how well-spoken he is oh my. The palatable black man. This is not a criticism of Obama, or that he should position himself as anything other than what he is. He did not grow up in the hood and to posture like that would be disingenous and detrimental to his campaign. For all the excitement I have about him, his meteoric success is a sad indication of how far we have yet to go in this country.
An Ergodic Walk 
I’m not sure I really get what your complaint is. What would Barack Obama have to be for you to believe that his success is indicative of meaningful advance? I don’t think you meant to say that Obama is the cute little black boy from an ’80s sitcom all growed up. But that’s kind of what it sounds like.
Part of the reason for his success among people who hadn’t heard of him is precisely that he’s like Webster, as you point out. Not that that is what he is or how he actively portrays himself.
I mean, it’s an unproveable hypothesis of mine, but I think his biographical background influences people’s view of him more than his achievements and policies, especially among those who are unfamiliar with him.
Having something to latch onto isn’t bad though…