A major reason that some digital listening disappoints those familiar with analog is the very poor analog section even in some of the most expensive DACs. They often compare VERY unfavorably with the "analog section" of a phono pre, which is to say, the phono pre itself. But they are there to do a similar job.
A DAC may have a sophisticated digital section providing apparent transparency, space and dynamics to a bunch of instruments that seem themselves to be made of cardboard. And some listeners think these DACs are great--especially after good reviews. Without providing as much in effort to the analog section though, the DAC will miss the harmonic richness and depth of sound we usually attribute to good analog.
From the point of the DAC maker, most of his potential customers may have never heard a musical instrument except through a loudspeaker. So some multi-kilobuck DACs use chip op amps costing a buck or two at the center of their analog section. Call me cynical.
Replacing chip op amps in DACs of all sorts
with good discrete analog sections
has become a hobby to some and a profession for others.
So, if you're an analog person, as I am, don't tell me of your disappointment with your expensive DAC. Look inside first. Then we can talk.
And by the way, while amp and preamp manufacturers are pleased to tell you what's inside their cases, DAC makers often are not. Rather, they often try hard to hide what's inside. As do many of the reviewers.