I have given this some thought myself. I do have a bryston amp and pre-amp that are about 20 years old, and they are good enough for me. For DACs, I presume their technology is advancing quickly like computers and the value equation favors the current models.
I cant see myself buying any linear amps of any sort since class D has become mainstream. I got an edge a2-300 from ebay for $250 and it sounds surprisingly good to me, so that is the technology I will explore when I upgrade.
Due to the natural progression of my career and children now adults, I do have the money for a lot of those dream items from the 90s that are to be had on ebay, but class D is where I am going forward.
I am also seeking to go with balanced from pre to amp, so that rules out a lot of old amps and pre-amps. My bryston bp 25 has this covered, but at some age of gear, balanced was not implemented at all.
Back in the day I had a threshold stasis amp that was pretty nice, but I sold it. I thought about getting another one, but those are pretty old now and I wonder if the power supply caps can be replaced with new and the solid state devices, and unbalanced, to gonna keep it in the fond memory location.