I would the iPod Touch. I bought one and I don't regret it one bit. At first, I jailbroke it. Very, very simple process. It's great to have it jailbroken, free apps and stuff like that. One day, I decided I wanted to upgrade to official 2.0.2. All I did was connect my iPod to the computer and then just press restore. It automatically restores the firmware, OS, and all files on it to factory defaults. What I am trying to say with this little "story" is that it is extremely easy to use the Touch and is very customizable. The Zune, not so much. Plus, with the advent of the App Store, you can get free (as well as paid apps) on to your iPod legally. Don't forget, many games are coming out in the App Store for iPod Touch/iPhone like Need for Speed: Undercover (the graphics are simply amazing), Spore, Crash Bandicoot Racing (also amazing graphics).
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