ipods are a complete con imho, they try to force you to use itunes as your complete one-stop music solution, when what you actually want to do is browse what actual mp3 files you've got on your pc and copy, delete to mp3 player and burn at your leisure. The whole ipod/itunes philosophy is if you don't do EVERYTHING using THEIR system, they're not playing ball.
itunes tracks use their own custom encryption to make it so that you can only play it on an ipod or the computer with itunes on. So are wmas from things like napster, but you can get software to unencrypt them to standard mp3s.
That'd be ok if it all worked flawlessly. But i've heard nightmare horror stories of people getting into shockingly confusing tangles trying to transfer tracks when they do something so simple as change their pc.
Also, ipods' hard disks wear out (they're not all solid state), this happened to my dad's one. You switch it on and it's got a
face symbol, so although without inetnding to imply it's intentional, it's obviously something that's envisaged is going to have a shelf life! I've also read stories of there being issues with the batteries and screens.
My advice is get a decent solid state (memory card based) mp3 player, sign up to a wma shop like napster or nokia music store or the equivalent, bite the bullet and lash out on a wma to mp3 converter, and manage your music using windows explorer. It's the only way to be completely fuss-free.