You seem to assume that an individual's personality can only be made up of actual experiences. But Obama's book Dreams from My Father is entirely about the attitudes and resentments he took on based on his father's experiences and those of Africans and blacks in general.
Obama is a mixed-up mess of envy and resentments he's taken on from various aspects of the black experience, and the Third World experience, few of which he actually expereienced in any real way while growing up, and certainly not while he was given affirmative action access to educational oportunities he had not earned based on merit.
But still, he's taken on those resentments and attitudes and the attitudes of the street thug is often a part of it.
No, it isn't -- my point entirely about "sprayed-on" toughness. Real toughness, though, goes to character, and that is acquired through experience, good or bad. People who haven't had it tough aren't tough, is the way to say it.
As for all the rest, you seem to be agreeing with me about its artificiality. If Obama really represented his background, he'd be a go-along guy minding his own business. The interventions of others -- FMD, Red Mommy, Red Granny, all the rest -- certainly account for changes in him, but I don't see anyone in his background who will have imparted the kind of personal tough-guy attitude that someone who'd been up the river for 15 years brings to the table from experience.
Someone went underground once, long ago, with the Weathermen for several months, in order to write an article about them (don't remember where -- it might have been Rolling Stone), and his insight was that Ayers, Boudin, Gold, and all the rest were suburban kids trying to learn to be tough by living rough and not doing the dishes. But they're not the same thing, and he doubted they ever really imbibed the kind of toughness prison and genuine privation impart.
That all said, the most murderous thugs in 20th-century history, at least on the Left, were all middle-class darlings who got their Rad.D. degrees at the Sorbonne or someplace, and then went out and killed a million people in the name of Marxist-Leninist revolutionary principles.