Its a horrible question to answer this one because I feel that the audio quality of converters is a very subjective thing. Its a matter of taste. I can say this - i've tried to read as much as I can about converters after embarking on the RKN AD/DA project on this board which has taught me a bit. From what I have read, the keys to converters are:
1) Op amps in the analogue path.
2) The power supply.
3) The chips.
It seems that really high end converters have sorted out the analogue path and power supply issues that plague most prosumer gear, yet the chips are often very similar if not exactly the same in both units.
So if the only difference between the gear of 2000 and 2011 is newer generations chips, I would contemplate not enormous differences between them. If the difference between these units of 10 years ago and now is different analogue circuitry or ripple free power supplies, I would think they would be way better. I don't really know the answer to this. Just my ruminations and observations. I can say that its worth trying to hear a difference between the Apogee Symphony and Duet 2, since the Symphony was the unit chosen as the best by a group of listeners in the AVID blind test I mentioned earlier and attended. If the Duet 2 sounds good relatively in comparison to the Symphony, it would be pretty amazing. Of course it wont sound the same, but if the results are pleasing after hearing the Symphony, you're onto a winner in my opinion.