Interesting observations. I think Obama despises Romney because Romney is everything Obama can never be.
I think that Obama can never be anything except the personas he takes on or is given, because he is essentially an empty void person. People like that are also prone to drug abuse to escape their own emptiness and lack of self-identification. They are also prone to going into the acting profession in order to “be someone”, and as adults, have it legitimised by getting paid. They are eternally taken with themselves because they are eternally trying to figure out who they are, because they are essentially “nothing”, and who could ever admit that to themselves and not commit suicide?