Tilt Gore. Even outside the crash Bush's unpopularity still would've been a problem.
Mostly because of Iraq, it seems. However, even a popular two term president doesn't automatically translate into a victory of his party's nominee. See Eisenhower, Clinton and Obama, who were all solid above water on the eve of the election to pick their successors. 1988 is sort of an exception, though I think even that one was winnable if Democrats chose a better candidate than Dukakis.
The Democrats could have won in 1988. However, I think their field that year was fairly poor. Gephardt or Gore would have done better but would have still lost imo.
If Bush isn't the nominee then I think the Democrats are probably favoured to win even with Dukakis, as A) Bush was clearly the strongest candidate the GOP had and B) if the incumbent VP is losing the primary, bar exceptional circumstances, that means the party is probably in trouble