Has there ever been an administration in the USA who seriously tried to change the way elections are handled in the USA? Especially the fact that more populous states are underrepresented in Congress? It would seem like an smart move, especially as the Democrats have a very hard time winning elections because of that.
How are more populous states under represented? They get more congressional representatives. And what does the Democratic Party have to do with it?
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Especially the fact that more populous states are underrepresented in Congress [Senate]?
That's the one part of the Constitution that's still impossible to change by amendment (originally there were 3 but the other 2 expired in 1808).
Article V - Amendment
... no Amendment which may be made prior to the Year One thousand eight hundred and eight shall in any Manner affect the first and fourth Clauses in the Ninth Section of the first Article; and that no State, without its Consent, shall be deprived of its equal Suffrage in the Senate.
So trying to change the composition of the Senate would be quixotic at best.