On the discussion that broke out of any George W Bush political career if his father is not elected President in 1988, check out this:
https://en.wikipedia.org/wiki/Ben_Quayle
George W Bush ran for Congress in 1978. Texas adds tons of Congressional districts every census and gets steadily more Republican up to 2016. George W Bush would have no problem with a federal Congressional career at least if he wanted to. Look at some of the Republican Congressmen that did get elected from Texas in the last three decades.
An idea I do find interesting is if Bush Sr wins the 1996 election after eight years of Cuomo. How would Bush's Presidency be different without having his father's Gulf War legacy to contend with, and without Cheney as VP? Would 9/11 still happen?