IMO, this is the first time in BHO's life that he's actually had to face work and reality. Sorry, but he's a spoiled brat whose worst hardship is being half-black...and that really shouldn't be one.
I think you are right. He had no idea he would actually have to do stuff. He would just float all the way to the WH on his skin tone. He has never known anything else, so why would he think this would be different?
I think there is some truth to that. However, I would phrase his problem as "not having faced adversity." (He can play the race card all day long, but, in fact, his skin color has helped him more than hurt him.) You can tell he does not deal well with adversity because he gets petulantly defensive and obstinate when he is criticized. I would not be surprised to witness a public temper tantrum or breakdown by Obama by November. I think he'll eventually crack under the pressure--hopefully in public.