Bush 41 lost in 1992 because (A) he was perceived as indifferent to the plight of the unemployed, (B) he was blamed for the export of American jobs at a time when people were becoming very conscious of jobs being shipped to foreign countries, and (C) he angered Ross Perot, a person with a constituency and the money to bankroll a campaign.
There may not have been a Gulf War if Dukakis had been President. There would not have been the Perot candidacy in 1992.
This 274-264 map with a 50%-49% squeaker is the best I can see Dukakis doing in 1988. He would not have won a single Southern state in 1988.
If the economy was on the ropes and Dole was the 1992 nominee, the VP candidate for the GOP would likely have been CA Gov. Pete Wilson. Wilson was pro-choice on abortion, but the GOP would have worked something out to where that would have been smoothed over. There would have been no Buchanan candidacy, and there would have been no Dan Quayle.
Would there have been a fall of Communism in Eastern Europe? Would there have been a Gulf War? Would there have been the fall of the Soviet Union and a new Russia and a new multitude of independent states that were former Soviet Republics? Bush 41 was viewed as having shaped these events, which were monumentous and he lost anyway. Would there have been a NAFTA in the works? Would Dukakis be seen as the architect of NAFTA? What position would Dole take on NAFTA?
This would have been Dukakis/Bentsen's 49-48 victory map in 1992 over Dole/Wilson. The race would have come down to CA and TX. I believe that CA would have shifted to Dukakis, but I believe that TX would have shifted to Dukakis due to Bentsen.
That's if Dukakis did everything right. A more likely scnario would be Dukakis losing to Dole.
No one liked Dukakis. People were OK running with him in that he was relatively safe, but he generated no enthusiasm. People were only psyched about him because he seemed as if he could win. His diffident style cost him the election. His pick of Lloyd Bentsen was actually a blunder; he should have picked a VP who could have brought in his state for the ticket. Fritz Hollings or Sam Nunn would have been a better pick. If he had been elected, he would have been elected in a time of relative prosperity. What is questionable is the degree to which Dukakis would have been able to inspire the nation when times were tough. (America would have seen his "Massachusetts Miracle" come undone as President; in real life, Dukakis's approval ratings when he left the Governor's Mansion in MA was around 15%.).
So, no, I can't imagine Dukakis getting re-elected. That's because I really don't see him as having ever gotten elected in the first place.