I think the eighties fashion was to play on "modern" guitars : superstrats, steinberger, schecter, pensa, and all stuff like that
you can see that all guitarists during the eighties tried new gear, digital effects, etc... Gilmour played his BMG pickups strat with Boss stompboxes etc...
digital recording was the new technology, and all music business had the aim to get the "perfect sound"
and then, in the nineties, after Kravitz went back to analog, using old sounboards and vintage mics... after grunge artists came back to old stompboxes like big muffs, vintage guitars and all, then you saw "old" artists using old gear again. Mark got his 58 and 59 LP, the jurassic strat... Gilmour used his big muff again, many artists recorded analog again, inclunding Mark, etc...
it depends on eras. When EC bought his 6 fifties strats in late sixties, they were not expensive.
But now of course, a strat from the fifties and sixties have extreme big value. because many guitarists made the "vintage guitars fashion". One of the first was Page when he got his 59 LP in late sixties.
But at the same time, Hendrix didn't play on "vintage" strats. He played on guitars maded during years he was playing : you can see him with 65-66 strats in his early years, while he played 68 strats in woodstock and Wight