It occurs to me Trump is having fun in this campaign. Like most people, I instinctively like and tend to trust to a certain point people who know how to have fun. It implies at a minimum they are not OCD ideologues, and at best a generosity of spirit and outlook, that I think does genuinely characterize Trump.
Obama comes across as a sour-faced scold, does he not? Whatever the words he is given, he always turns them into a lecture about how bad you are and how good he is. Trump is more like “life’s great!!! Come join me on the podium.”