I think that George Bush means well, but has had it too easy all his life, he had wealthy parents who sent to the best schools, where he was well liked and relatively successful. When he got into the business world, he had enough money behind him to allow him to dabble in various undertakings without worrying about where his next meal was coming from if he failed. I don't think that it ever occurred to him that people would hate him for being who he is and he still can't believe that he can't turn them around.
Yes, that's part of the problem. Another, I believe, is his particular understanding of what it means to be a Christian.
Another problem is the country-club Republican mindset, which Bush Senior embodies and GWB has absorbed far more of than his fans think. The country-club Republican is not only a moderate at heart, but sees all politicians (except those on the "extremes") as being in the same business and having more in common than not. They look down on those who want their politicians to fight. It's pretty clear that W. thinks this way too.