Like most Mac users, I use iTunes to organize the music I have collected as files on my hard drive. It provides reasonably good support for setting up Classical Music playlists; and, while it does not handle jazz particularly well, I cannot say as I have any good ideas for how to do a better job without truly massive amounts of data entry. For all the virtues of iTunes, however, I have to confess that, in my history of using the system, I have downloaded exactly one track; and that was at the request of a friend.
I get a lot of my music by downloading these days. My problem is with the iTunes store. It is so geared to the iPod set that it seems content to disregard that there might be people who do not listen that way. Everything is designed around tracks, with no regard to how certain tracks are meant to be listened to consecutively, because together they constitute a single piece of music. There are plenty of other sites the show more respect for my kind of listening, and they general provide enough metadata to facilitate my importing their content into iTunes. However, the iTunes Store seems to live in a world of tracks and entire albums, oblivious to any intermediate groupings.
I suppose it comes down to the fact that this world is not really a world of listening. It is a world of providing auditory stimuli, a world in which shuffling tracks is more important that sustained attention over all of the tracks in a three-act opera. (Yes, I have wondered what it would be like to shuffle the tracks of Der Rosenkavalier on an iPod. Fortunately, it is easy for me to dispel those thoughts!) If that is the case, then serious listening may well become a lost art; and, if the people who want to listen to music vanish through extinction, what will happen to those who strive to make music?