It's amazing to me that after a decade and more of competition in the PC/Portable media market, we are still left with such shitty programs to actually implement our media libraries on our home computer networks.
I've always been an iTunes guy, as much as I hate Apple with a passion, so far they have always had the best program, and because they know they have the best one, they don't do a damn thing to improve it. Ever. It's starting to get old. I've recently begun to use Zune just to experiment and give the program a chance to make me happy, and so far I must say I'm disappointed.
The integration of Zune software with your Windows Live profile is pretty cool – from a social networking standpoint, ignoring the fact that they seek to find copyright violators as well as to rape the public with ridiculous song prices. Additionally, the ways in which you can view your media library are far better than iTunes. iTunes features no customization whatsoever on PCs, which I hate to break It to Apple, are the vast majority of their demographic – both for iPods and iTunes downloads, although I'm assuming it is still moderately malleable on OSX. The Zune interface is simply better – implementing aesthetically pleasing social networking, a strong juxtaposition to iTunes honestly terrible store-based web profiles which no one even cares about unless you're just that much of an Apple fanboy, which is pretty much anyone who has an Apple account and actually uses it.
Zune has a much better looking and smoother interface as well as a better social networking system. iTunes has a much better CDDB system which is entirely automatic as opposed to the crappy and mostly manual Zune system, athough in reality they are both terrible missing a lot of information, despite that my library itself should single handedly have accounted for at least 20% of the new CDDB information added to the system in the past five years.
It would be great if Apple and Microsoft worked on a joint project to make a media library program that worked with both of their mobile players, with their home media players (Media Center computers and Apple TV), and actually made the process of listening to your music and watching your videos enjoyable.