I don't see the anti-democraticness of the US Senate as an issue in either case, do you? Doesn't matter how democratic the Senate is, it isn't going anywhere.
However, the court has ruled that a similar situation in the states violates the equal protection clause.
Almost always, but electors had (and still have) a lot of power. You do end up voting for the elector, who votes for the person. And, yes, the system allows a loser in the popular vote to win the Presidency. It also makes races much closer than their popular vote would indicate (except for a few occasions).
But the victory margin doesn't matter. It's who wins. And the simple fact is that the popular winner almost always wins the electoral vote except for in a few very, very close elections.
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