My experience is that older DACs often have excellent power supplies and analog output stages. Those seem to be areas were designers skimp these days, especially with just using simple opamp output stages that measure great but don't sound all that amazing in a lot of cases.
On the other hand, older DACs will often be limited on their USB capabilities, if they even have one. Which can be overcome by using a good DDC to convert to AES or whatever you prefer.
I still have a Luxman DA-06 from over 10 years ago. Original price maybe $6k, now sells for much much less on the used market. I've heard it beat many new DACs, especially when it comes to midrange body, layering, and richness. Same goes for my ModWright Elyse DAC which replaced the Luxman.

