I made the 100% switch myself and I am also a heavy tech user, developing web applications for a living. iTunes? What about the plethora of media applications in a Linux OS? Banshee I hear is fantastic at providing pretty much all the features for an iPod you can imagine. Skype? What more features do you want in skype? You can web cast, conference and text chat. Do you really need the spangly new Windows interface that badly?
And you are right, typically a regular user can do it with no problem. My girlfriend took to Ubuntu like a duck to water with next to no hand holding from myself (I was away for the first two weeks she used after installation). If she can handle Ubuntu, then anyone can!
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