On questions of Constitutionality

Not legitimately, of course. Are you saying that a libertarian holding federal office (alas, state nullification is not viable these days) should not nominate/confirm originalist SCOTUS justices?

The original ratifiers were there only as representatives of their respective organisations. If these organisations no longer care about such points, then they are moot.

Okay, say a libertarian won the presidency and needed to appoint a SCOTUS justice. What criteria should govern his decision?

Whoever he thinks will be the best man for the job.

Yes, but how should he determine who is the best man for the job? Commitment to the original understanding of the Constitution and its amendments? Decentralism? Commitment to find some reason to argue against the state’s acts even if they were allowed under the original understanding?