Will we see more EC winners who lose the PV?

[Skill and Chance]

Yeah, almost certainly. The question is whether there will be a Democrat who wins the EC but loses the PV I guess.

Thus far all such examples involve a Republican beating a Democrat even though said Democrat wins the popular vote: Trump beating Clinton, Bush beating Gore, Harrison beating Cleveland and Hayes beating Tilden.

JFK 1960 was probably a Dem EC win/PV loss, depending on how you allocate the votes cast in Alabama where electors were selected in a very complicated way.

Regarding the future, it could plausibly happen in the late 2020's/2030's if Texas and Georgia are just left of the nation and Republicans are getting 10%+ margins in many of the big Midwest states.  Also helps if Upstate NY/Downstate IL is a GOP +25 blowout by then and/or if Florida is GOP+5 or better.  The tied PV map would be something like this:

[Skill and Chance]

It's interesting how similar 1876 and 2000 were and how similar 1888 and 2016 were.

Just curious, why do you say 1888 and 2016 were similar? It sounds like an interesting comparison.

1876 was in dispute and ended with people feeling it was stolen while 1888 was undisputed.

Judging by 2018 vs. 2002, I don't really agree with this.  Outside of the Dem base, most voters got over 2000 very quickly.