Anytime before COVID. Without COVID, Trump would’ve trounced Biden and quite possibly win the popular vote.
Trump would have lost in the 2nd half of 2017 andf through much of 2018. For late 2019/early 2020, I see a case to make he would have won the EC again. NPV? More than just doubtful.
Trump’s approval ratings were trending upward before COVID, and the economy, etc, were generally doing good. I don’t see why Trump wouldn’t have been able to win the PV, especially since incumbents are notoriously hard to unseat, unless they’re unpopular (even so, despite Trump’s unpopularity, Biden barely beat him. 40,000 votes in GA, AZ, and WI would’ve handed 2020 to Trump).