I have lived in both Indianapolis and Terre Haute and done extensive Scouting there. While living in those places, I noticed that inner city kids are often very out of place in the woods. This is not a thing to wonder at, I suppose. It's just not been part of their experience. Urban blacks, however -- both adults and kids -- seemed more uncomfortable with the whole camping thing than whites did.
It's a legacy of the African-American experience in the Midwest. Southern blacks -- who were in origin largely rural -- moved north during the Great Depression. The jobs that brought them north were in urban environments -- Chicago, Detroit, Kansas City, etc. Another factor in concentrating them in big cities was the racism (real or perceived) of small-town white America. The result was that within two generations, northern urban blacks were almost entirely divorced from their southern rural culture. They didn't farm, they didn't hunt, they didn't camp -- and they didn't feel secure outside of the cities.
(Affluent blacks established their own camps and resorts in the country, it's true, but many less well-off black children knew only city pools to swim in and sports played in city parks.)
The web of relationships that blacks have in places like southside Chicago is all-encompassing. Their churches, their recreation, their shopping, their schools, are all close at hand. There is no need to leave the urban cocoon -- and little desire to. This also means that -- if you care to make the attempt -- you can largely construct a life separate from white Chicagoans. You probably have to deal with them on the job and in public places, but after hours and in the home, you don't have to. And those whites you do associate with are otherwise pretty much city dwellers like yourself.
Now, Sen. Obama has lived many places. He ought to have wider horizons than the typical black from the southside of Chicago. Mrs. Obama attended Princeton; she's been places, too. But both have firmly established themselves in the matrix of that place, with those relationships.
Those white folks they do associate with regularly are very upscale, very educated, and very liberal. Lawyers, academics, politicians: a group whose social network and associated outlook are probably as limited as that of the good folks of Trinity UCC. It's a crowd that only talks to other members of itself.
The result is that Obama has had trouble identifying with small town Americans. As Mark Steyn points out, he talks about folks like us as if he were an anthropologist studying the natives of Papua New Guinea. Meanwhile, Mrs. Obama attempts to connect with economically hard-pressed folks by complaining about how they -- the Obamas -- are stretched. (This is a case which is hardly believable, seeing as how between the two of them they are making hundreds of thousands of dollars a year.)
The Obamas come off as visitors to America, tourists assuming that the rest of the world should be just like them.