From what I've seen, the job of community organizer is what we call a 'poverty pimp', which holds with my assessment of his character. He is too self centered and thin skinned to be effective at understanding the complex needs of mixed racial community. Even his pledges of unity "it's not about red states or blue states, it's about the United States" sound canned, the closer you listen the more you see the "sincerity" as faked.
I believe he is too self centered to even have a half brother, in his upbringing he was always the only child of what had to be doting grandparents. I don't think he can share a limelight. He surrounds himself with lesser stars with the exception of Hillary, people who are not inclined to say "Mr. President saying people can keep their plan when we know that they can't might not be a such a brilliant idea..."
I am confused too at his choice in a wife. It strikes me he would need some off line comfort, a place to retreat to like many powerful men. Instead he seems to have chosen an anger driven woman with vengeance on her mind and equally insecure. I never believed she actually care what other kids had for lunch, but they needed a 'first lady issue' to make her look like Jackie or something. She's something of a war horse with the class and taste of a farm wife while he exhibits a great character and excellent taste, the man's suits and the way they hang on him are to die for.
"Small people talk about people, average people talk about events, great people talk about ideas" Eleanor Roosevelt