So let's bring this to the present. What if the 1929 act never happened to lock in 435 members in the House, but instead codified what had been common practice since the Civil War.
In the 2010 Census only MI lost population and loses 2 seats as NY is the last to be brought up to their status quo. AK moves up to 3 seats, leaving only VT and WY with 2, so DC continues to get 4 electors. There are now 1140 members in the House and the average district has 270 K inhabitants.
In 2012 Obama wins the EC by 780 to 464 (1 EV from NE).
In 2016 Trump wins the EC by 705 to 539 (Trump gets 3 EV from ME and loses 2 in NE).
In 2020 Biden wins the EC by 713 to 531 (Biden gets 2 EV from NE and loses 3 in ME).
Though the expanded EC matched the popular vote winner in 2000, it would not in 2016. The senate seats in the EC don't impact this result either. It looks like this the sort of case the EC is meant for - to work against a candidate that relies too much on a regional base, regardless of popularity.
Decided to assume the district breakdown as 2016 for ME/NE rather than calculate manually, but this was inevitable.