One important thing to realize about the latest generation of music servers is that they have made considerable progress in enriching ones listening experience with information (referred to as "metadata"), similar to how it used to be with vinyl, where a nice album cover and package made the overall experience more enjoyable.
That aspect of things took a dive with CD packaging for obvious reasons, and is probably still teh biggest practical drawback to CD format.
Take a look at the latest PLEX music server for example. Once music files are tagged with basic artist and album information to identify it correctly, PLEX is the first solution I have seen that may cross the inforamtion threshold that vinyl packaging used to provide, and deliver an even better and more extended and enriched listening experience, not just in one's home, but mobile out and about as well.
I feel like things are finally moving forward to some extent now with music servers, and that a lot of teh wheel spinning with the technology that naturally occurs early on is now a thing of the past.