I have the perspective of a long-time audiophile (40 years!) and as a 10-year dealer in a few great brands. Clients and customers often call or email me asking how a given DAC sounds. Some give me subjective descriptions of their own gear and why they feel the need to change or upgrade, and then they ask me for subjective comments. Instead of volleying with subjective comments, I recite specs, measurements, and dynamic capabilities for given types of equipment. I sometimes recite things about headphones that are really just the frequency response graph put into words.
Most people who start the subjective conversation with me seem to get the hint that I'm not in that game, or else they continue giving me their own subjective impressions of things -- which is fine, doesn't bother me to hear how they feel. When presented with the bald question "does it sound great?" or "how does it sound?," I answer that of course it does or I wouldn't sell it! I also use the car saleperson line: "I drive one of these myself." Which in my case, since I shuffle through units all the time, is totally true!
Personally, since the advent of digital -- I had a Sony CDP-101 back in 1983 -- I have preferred to stick with digital and upgrade periodically as developments warrant. Having suffered through analog, I would never consider going back. Even the first-gen CD players sounded better to me than the best analog playback equipment I had access to in 1983-87. I would never go back to ADS L1290's, or Celestion 700's, or even B&W 802's (gen. 1). They were all great in their day but, to my ears, pale in comparison to lower-priced versions today.