How old is too old for a Dac?


Been out of the loop for a good bit, and wondering how much things have changed in digital. In other words, how old is too old for a dac?
spoogemonkey
I believe that for redbook CD playback via transport or as uncompressed files from computer or server, use of an older DAC with an excellent power supply and analog output stage at a fraction of original cost seems appealing to me. Of course, with the computer use of a USB/SPDIF converter would be required.  I am about to try a used Bel Canto DAC2 in my secondary system.  Currently use a Bryston BDA-1 in my primary. 

As Bigkidz stated, considering DSD digital is different. 
H I Jond,
What differences are you hearing via further listening to the Audio Note and the Yamamoto DACs?  I'm assuming this was a fun and informative comparison. 
Charles 
Charles to be honest the AN keeps getting better by the day I haven't been able to take it out yet! I I am pretty convinced the AN is considerably better than the Yamamoto but hearing being fickle I will give the Yammie one more listen before I decide.  Off to NYC for the weekend so that will likely be next week or weekend.  There is just something so right about the AN though I feel very fortunate to have won that auction now!
Cheers,
Jon
Jond,
I'm not surprised that the Audio Note is impressing you,  it has been highly praised for many years.  Excellent design and implementation withstand  the test of time. No doubt that using Duelund CAST as my output coupling capacitors improved the Yamamoto DAC further.  I'm certain that I'd be just as impressed with the AN DAC as you are. Congratulations. 
Charles