George Bush was a terrible president. However in some ways he was a breath of fresh air because he wasn't racist or sexist. He had two African-American Secretaries of State and a Latino Atty. Gen.
While George W was president we would always hear comments from individuals close to the Bush family that said Jeb was supposed to be the next Bush president, not George. The problem is that Jeb has to get elected. And when Trump went after Megyn Kelly and talked about words he'd used to describe women, Jeb should have been all over him for denigrating women. But instead he continued to stand there like a man who wasn't quite comfortable with the debate.
It has taken Jeb four months to say he would not have invaded Iraq. (a duh, did you think no one would ask that question?) He has moved to the right in order to pick up support and people don't seem to be that impressed with him. He is advised by the same people who advised George.
When George won the nomination and the election, people at first felt comfortable with him. He was "a good old boy" in a way that wasn't that offensive. But Jeb looks uncomfortable and I think that's a problem. Perhaps he would be a better president than George, but first he has to win the election.