I do not own an iPod, nor have I ever used one. But they use a different format from other mp3 players, so I suppose that you need to use iTunes to convert existing mp3s to the correct format. Stuff downloaded from iTunes is not in mp3 format and there's some limit to how many devices you can transfer downloaded tunes to. I only use iTunes for podcasting, as it will happily go and find the latest versions of all the R4 progs I think I ought to listen to but never get round to.

Personally, I'd avoid iPods like the plague, but that's my personal opinion, as I prefer things to be compatible with as many other devices as possible and don't like having to have loads of different formats. However, SiL got a 30Mb video iPod for Christmas and I can make enquiries about it if you like.