It's an old standby of American politics that the VP choice makes little difference electorally speaking, and I'm inclined to think that would hold in this alternate scenario as well.
That said, a ticket with Trump would definitely be seen as a novelty, and not in a good way. It MIGHT call into some question GHW's judgement.
Plus, I don't think Trump in '88 would have had the same conservative street cred that Quayle had, and which the alleged closet-liberal Bush needed to bolster his right-wing flank. With Bush already known to have been previously pro-choice, Trump's general aura of the Manhattan party circuit might not help matters.
Now, THAT said, novelty and NYC hedonism didn't hurt Trump at the front of the ticket in 2016, so I guess it's possible that they wouldn't have done much damage in '88 either. Though this time around, the ticket also had Pence on board to appeal to the Christianists. In '88, the ticket would be the guy who steadfastly refused to call himself "born again", along with a guy who would probably turn up in most people's mind's eye when asked to envision "coke fueled orgies in Manhattan discos".