Zune HD is without a doubt the best thing since sliced bread in the portable music category. Plus you can get the subscription service and download any song you want.
iTunes took 45 minutes to install on my gaming desktop and almost all my games load up faster than it does. No program that heavy and slow should ever been required to use a portable player. If not for that and the DRM, I’d recommend Apple but since you’re buying the entire package I have to say Zune.