I feel like one of W's problems was that he had an underlying insecurity to him. Remember, before he ran for Texas Gov, he'd largely been a professional failure. So when he becomes leader of a post-9/11 free world, he surrounds himself with strong-willed people who constituted a chorus of "Mr. President, this is your hour" and so he was provided the confidence to make terrible, terrible decisions.
Trump completely follows his own internal compass, and he has demonstrated over and over that his worldview is pragmatic more than anything. The only thing he cares about is doing what it takes to win. He knows how to read his audience and adapt, so when it's kosher, he's pro-choice, pro-universal health care, pro-gun control, but when he needs to appeal to Republican idiots, he's a xenophobic, bible-thumping birther.
So I don't think he's going to launch some ideological battle because he has no ideology. And then he'll start throwing out all kinds of asinine proposals that Congress will shoot down, and then he'll call Boehner a "chain-smoking sunburnt salmon" and Harry Reid will be called a "total loser who couldn't get laid at Dewey Beach on Labor Day" and I will be entertained while everything burns forever.