You nailed it. The only versions of America Obama knows from personal experience are Harvard and the South Side of Chicago. Neither is really typical of the rest of the country. He's now playing catchup in all sorts of areas, but there's no substitute for having actually lived among the people and imbibed their view of reality.
You know: Mexican kids sing in Spanish while wearing serapes and sombreros and shaking maracas, while Dutch kids have wooden shoes and Indian kids charm cobras out of baskets while playing a flute.