The value of "Legacy" DACs vs new?

Everyone points out that digital technology is constantly advancing at a pretty rapid pace. So where does that leave something like my six year old Wyred4Sound DAC 2/DSD?

I like it a lot, although it's past time to upgrade. But is it a SQ dinosaur?

It's probably worth $500-$700. There seems to be many DACs in that price range.or Streaming DACs/All-In-Ones for a bit more. But they are generally loaded with features that I wouldn't want. Like MQA, Dirac, HP amp, PHONO, RoonReady. etc I'm a minimalist, who is definitely most interested in SQ. .

So... as a VERY GENERAL rule-of-thumb, for NEW equipment, what price range would you say that I should look in?

I hope that it's clear that I'm not really asking for brand/model recommendations, or something like "just shop with you ears". At this point I am just asking for more general comments,,,


There are some DACs that still use the ESS 9018 chip that's in yours. You could get a DAC with the newer chipsets I'm not sure how much better they would sound. 
Agree with djones51, although I’ve owned two devices with that chipset (Mytek Manhattan and Oppo 105) that sounded vastly different from each other.  Newer may not necessarily be better.  It may be different, because different DACs tend to emphasize different aspects of music...
W4S might have done a better job implementing the 9018 back when , than some do now with the 9038. The 9038 has a known issue with a "hump" that needs to be addressed some companies have done a better job than others. The Benchmark DAC3 still uses the 9028. I think Mytek still does as well?
chipsets don't drive the sound of dacs by themselves

a lot around them, both on the incoming and outgoing side matters just as much, if not more