I'm not going to lie to you: some stuff just isn't coming with you. Your DRM-ed AAC audio files, iTunes movies and TV shows, and even those iTunes audiobooks, just can't survive outside of the iTunes/iPod universe. So quell those fantasies of uninstalling iTunes, because you'll still need it to play your protected iTunes purchases.
The good news is, most everything else from iTunes is fair game, including your unprotected AAC and MP3 files, podcasts, unprotected videos, and playlists. Even your iTunes Smart Playlists can be reconstructed with a decent resemblance.
To see how it all works, check out theand I created to ease the transition.
If you're a Zune veteran with more tips to share, please feel free to add them in the comments section.