Dukakis had this strange idea that he was JFK's Second Coming-a Massachusetts politician with a Texan running-mate launching a Democratic renaissance after eight years of Republican plague. Since Carter had crashed so spectacularly, and an 1964-style victory impossible, Kennedy seemed the model to follow. Democrats only wrote off the South after 2000, and early on Dukakis was actually competitive in border states.
When I look at the 1988 map, it's so bizarre to see WV Democratic but not Vermont, CT, MD, and DE.
Not really bizarre. Back then, West Virginia used to be a Democratic stronghold (in fact, WV was one of few states carried by Carter in 1980), while Vermont did not start voting Democratic until 1992.