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[A18]

The west backed Wilson, but that was a one shot deal. They usually voted Republican.

[A18]

Demographics are different (very, very different in places), the parties are different, the issues are different etc.
Everyone that voted in 1916 was dead by 2000

Not necessarily.  If you were 21 in 1916, you were 105 in 2000 which in not entirely impossible, though very improbable.

I think some states allowed you to vote at 18 well before the 26th amendment was enacted. I don't know if that was true in 1916, though.

[A18]

Wilson was considered a progressive, and by most measures, he was. He greatly expanded federal power, started the income tax, and kept hiking it, started the estate tax, etc.