If you flipped all the states Dukakis lost by less than 10 points in 1988 this is the map :
by 1992 Allocation those states are worth 275 EV. After an economic recession which would take place during his presidency(for Obama in 2012 it began in the bush years), the early 90s crime wave would absolutely mean that he’d have to basically pull an inside straight again to even beat A Dole/Deukmejian ticket .
I think more likely is it would resemble 2016 and 2020 where Dukakis like Trump pulled an inside straight to win the first time but despite facing a bland old candidate would face an tough path to being re-elected from day 1(and Dukakis unlike trump has far less room to lose) and a recession would make that even tougher .