C# would be a good start, but I wouldn't go in to the XNA game development. That can get complicated really quick, especially with no experience in programming or graphics programming like OpenGL. If all else fails, teach him how to use Linux and C/C++/Java!

Chris, I have both a 1st gen Zune 30GB and a 3rd gen iPod Nano. I got the Zune first and never had any problems with it. However, I succumbed to the peer pressure of Apple and got the iPod Nano when it was released. I hated it. The iTunes software is bloated and resource consuming. It would take forever to load and was very slow to get anything done. Recently, I switched back to my Zune when they released the Zune 2.0 software and the Zune Pass. I havent touched my iPod since. The new software, even though it is basically a re-skin of Windows Media Player, runs perfectly on my Vista system. The Zune Pass is the best part if you are going to be purchasing your music through the device's software. It's a $14.99 subscription and you can download as many songs as you want. However, some songs, mainly those just released or labels that don't have Zune Pass DRM rights, can only be purchased with the Microsoft Points. With iTunes, the cost is usually $.99 per song plus any applicable taxes and there is some cost discount per song if you buy the whole album. The only thing you would have to worry about is if you use a Mac because the Zune Software is Windows only. But if you are like every other Mac user I know, you have Windows on Bootcamp or Parallels/VMware Fusion. I would also like to comment on some of the features you noted: Wifi - the wifi lets you sync over a wireless network and 'squirt' songs and pictures to other Zune users around you Radio - the built-in radio is a good feature as opposed the the iPod addon WMA - better compression, I think? Price - lower is always better Longer battery life - the best way to get the longer battery life is to turn off the wifi when you aren't using it and let the battery completely die before charging it. Good luck with your choice! Ben