Seems the question is this: Given the inevitable improvement in technology, do I go "all-out" on the best possible DAC or get a more reasonably priced DAC and replace more often?
I'll offer some insight based on a conversation I had with a tech at Ayre. His view is their new CODEX ($1800) sounds better than their older QB9 ($2900). The simple interpretation from that would say that the "reasonable and replace" strategy has merit.
Having said that I have seen reviews that dispute that SQ statement and reviews that support it. And I fully expect the "Ayre just wants to sell more DACs" comments so have at it.
As for me, computer based audio technology is moving fast. When I bought my QB9 there was no Roon and no Tidal, and DSD downloads were a gleam in the eye. So, I go with the "reasonable and replace" strategy. Too bad my definition of "reasonable" isn't a $32k DAC :-)
And I think mesch is correct in his post. Buying a good used one is the most bang for the buck unless you need the latest bells & whistles.