Is the Popular Vote unwinnable for the GOP?

[Virginiá]

I think it would either take a substantial shakeup in the coalitions or a term-limited Democratic president presiding over a recession at the end of their term (like Bush). Perhaps not necessarily a recession even, but some combination of events that causes the outgoing Democrat to be very unpopular. Maybe a relatively popular Republican incumbent president as well.

[Virginiá]

I think we are overlooking that Trump is from NY and NY has a strong pro-incumbent tendency to boot.  If the 2020 Dem doesn't also have NY ties like Clinton did, the state could trend pretty hard to Trump.  Trump only losing NY by say 12% in a close 2020 election vs. 22% in 2016 would be a game changer in terms of the PV.

The last time we've had a Republican incumbent president run is 2004 and Bush got blown out by 18 points. All things considered, there doesn't seem to have been any advantage for Republicans.

I don't think Trump is going to come close to those numbers in New York. They don't seem to like him, going by his approvals.