Great to have you back blogging.
I think the Obama’s problem is that in trying to close the gaps of perceived inexperience or being “different” he sometimes comes accross too presumptious. He is not helped by the media fawning over him not neccessarily because they admire him but probably because he makes good copy.
I think he needs to mind the gap but at times in life just do what you believe in and let the paradox takes care of itself . There is much to admire Churchill in this regard.