iTunes vs Zune vs Songbird: Music Organizer Showdown
Zune
Ahh, yes. Microsoft's answer to Apple's iTunes-if-we're-not-talking-about-Windows-Media-Player. Like iTunes, you won't be able to use the external-features of Zune with any device but... the Zune. Go figure. However, unlike Apple's iTunes, Microsoft has really hit one out of the park from an interactivity standpoint. Zune is easy to install and setup, and it works wonderfully with your preexisting music libraries in Windows. Provided you've dumped your music according to Windows' design, you won't have to go through any annoying re-importing via Zune.
Awesome
Interface: ‘nuff said. With beautiful backgrounds, fading windows that pop up and down, and awesome auto-collages of your entire library's cover art--to name a few--Microsoft's interface for Zune is simply amazing. It's responsive, it's artistic, and it's a lot more fun to navigate than any other music organizer out there.
Social Interaction: Since Zune ties into your existing Microsoft Live account, you gain access to a wealth of awesome social features that you don't normally find in music organizers. Track what you're listening too, message your friends and see what they're listening to, and gain mini-achievements for your rocking out!
Home Page: That's right. The Zune software comes with its own "You just loaded the app" page that gives you quick access to bands you've selected to care about, music you've recently imported, and Smart DJ mixes that--in theory--should give you the same kind of sound as the band you've selected.
Unfortunate
Limited Ripping: You can only rip tracks from CDs to a WMA or an MP3 format. That's not a lot of choice.
Zune Pass: Microsoft is really pimping its Zune Pass service all over the software. While admittedly neat--unlimited access to all music on the Zune Marketplace for $15 a month--I don't need it thrown in my face every time I'm trying to play a song or mix.
My Library? Zune Marketplace? Whenever you click on related links to what you're listening to, you might be pulling up a preview track from the Zune marketplace instead of an actual related song--e.g. clicking on Sara Bareilles when listening to Ben Folds could get you a 30-second preview of "Gravity" instead of an actual Bareilles song in your library. Zune needs a way to restrict recommendations to offline-only.
Long Loading: I'm currently sitting at 2.5-hours and counting just for Zune to make a Smart DJ mix of my files. While this will hopefully offer stronger musical recommendations than iTunes' default "eh, whatever" DJ service, you'll want to make sure you enable this functionality... a few days before your party.
Crazy networking: Streaming audio files in iTunes is a breeze--just click on a shared computer and play away. Zune requires you to go through Windows Media Extenders. Admittedly, this opens up your software to more devices for playback. However, it's a bit more involved of a process than iTunes--also, no Zune remote software for your device or wireless speaker connectivity.