Yes, actually. His parents were a Harvard alumnus and a mother who was both gifted and accomplished in Anthropology (with a wide network) and the people who raised him from age 10, his grandparents, were hardly "middle class" in the one-breadwinner-midwestern-auto-worker sense of the word. They were at minimum on the affluent side of middle-class.
So, Obama's childhood is not even close to being typical. He started with a leg-up that only got better as time went along. About the only true obstacle in his way has been his race--which is decidedly a huge one to have overcome, especially in America, where racism is still deeply embedded in our society in a number of ways, and was much much worse during his formative years. But his economic and family environment put him way, way ahead of even the typical American's.
How many thousands of people had a Harvard alumnus for a father and gifted and accomplished woman for a mother? How many of those thousands became president?
Your second question is entirely irrelevant in the context of this discussion. "Become President" is just not a reasonable minimum measure of "success."
So, Obama's childhood is not even close to being typical. He started with a leg-up that only got better as time went along. About the only true obstacle in his way has been his race--which is decidedly a huge one to have overcome, especially in America, where racism is still deeply embedded in our society in a number of ways, and was much much worse during his formative years. But his economic and family environment put him way, way ahead of even the typical American's.