OP, I think in your speaker case almost no question that the older speakers would sound better… assuming they were of the same sound family (so you are not deciding on a different kind of sound). Construction is very important in speaker implementation and $6K vs $2K is a whole different category.
If you get into audiophile equipment, they are so well designed and constructed they are going to far outperform mid-fi stuff almost forever. I bought a top of the line Onkyo (mid-fi) tape deck in 1980… After a while I took home a first generation Nakamichi (first of the cassette decks ever made)… it was 8 years old (ancient in the rapidly evolving new tape deck market). The Nakamichi was so much better than the incredibly well reviewed and celebrated Onkyo it was as if it was a completely different technology.
This is largely the reason that high end equipment has no new model every years… thoughtful designs with outstanding components. A twenty year gap is too big, but under ten, older high end will likely best new, in expensive.