First of all let me start by saying how true the following statement is:
�iTunes is for people who like certain musicians. Zune is for people who like music.�
Sadly there are very few people who actually like music and most of them like �certain musicians�. However for MS to break into this space I think they are doing the right thing. First build the brand among music enthusiast. I am not sure how successful they have been with that. Anyway I do agree that music discoverability in Zune is much better than iTunes.
Secondly I too face the same problem with Zune pass. There is just so much that I end up downloading a lot of music and then some of them get lost. I think there is a great opportunity for the Zune team to innovate here. There has got to be some features or some way of discovering music from your own library. I would really hate to see them bring back the start rating system to solve this problem. I think there should be some sort of tagging system jut like we do with pictures. Maybe they should start to show �related artist� from ones own library. I really think they can innovate here by making discoverability of music from ones own collection easy and simple.
The Zune 2.5 update was good and I like it so far. It is also great to see two update cycle namely spring and fall. I am wondering what they will add in the next one considering a lot of missing features has been added.