I think what this thread shows is that some like digital a lot more than others and some don't like it all. It's likely a physiological thing.
It’s always a psychological ‘thing’. Psychoacoustics is the very basis of hearing and the stereo illusion. Giving meaning and context to 2 discreet sets of sound pressure waves in time is entirely psychological
As regards digital vs analog, you’re looking at a very mature, fully developed technology (analog) vs one still in the early stages of its development (digital). Early stage digital wasn’t particularly alluring, sound quality wise. What’s holding digital back is the getting-on-for universal belief that a recording that is a bit perfect copy of the original is as good as a particular recording can sound. What a lot of people haven’t realised is that a bit perfect copy can be GREATLY enhanced, while still remaining bit perfect.
Let me try to illustrate the point in a less (some will argue more) abstract way. Imagine the bits are sugar crystals. A crystal = 1 and no crystal = 0. Bit perfect would look at the pattern of crystals and decide if the pattern matches the originating pattern ie is the copy exactly the same as the original?. Back to the IT version of bits, logic tells us that as long as the 2 versions (original and copy) of the bits match exactly, everything is fine and can’t be improved, for that file. In IT, that’s correct. All a computer needs is an accurate file and the integrity of the data is maintained. That’s the basis of all networking. To end up with an unaltered copy of the data.
Back to the sugar analogy, as long as we’re only considering the bit structure, the IT concept works perfectly. But if we actually consume the sugar, then suddenly the actual content of each crystal plays a role. If there’s an off-flavour in the sugar, the data integrity may be fine, but the way it feels on our taste buds isn’t good and in order to make it taste good we have to find a way to purify the sugar.
In audio, we start with a file, process it in a myriad number of ways and end up with a file that if bit perfect, has exactly the same structure. From an IT perspective, that’s job done. But if along that processing we have introduced a number of impurities, when we consume those bits, they won‘t taste as good (sound as good). This is the HUGE difference between IT and Audio. In IT we consume those bits as data so the final arbiter is data integrity. In audio we consume those bits as sound, so the final arbiter is sound quality. You can measure data integrity. You can’t measure sound quality. One is an objective measure and the other a subjective measure.
The big difference between analog and digital is that in analog the original signal can only be protected and nurtured, whereas in digital the signal can be cleaned, refined and improved. The network is a way to move data files around, a good network does so with data integrity. From an IT perspective, that’s all that’s necessary. But if that data file is going to be consumed as music, the network can also function as a means to clean and refine the data stream and all I’m saying is that the cleaned and refined version of that data stream sounds (tastes) a lot better than the unrefined but non-the-less accurate version.
Coming back to the above point, the more refined the bit stream, the more enjoyable it is. If people know more about protecting an analog signal than they do about refining a data stream, it’s very likely they’ll prefer the analog. On the other hand if someone has truly grasped how a data stream can be refined, that refined stream can sound absolutely gorgeous and will likely be preferred over the analog.
Finally just to mention that DACs have a major role to play in how much the bit stream quality affects the final sound.