ipod - Itunes Music

Hi guys,

I am having trouble transfering my music to my ipod. Im using Ubuntu 11.4 and I have tried gtkpod ipod manager and Rhythmbox. For some reason only a small handful if my songs actually transfer. I'm trying to completely avoid using Windows on my home computers if possible.

Can anyone tell me why this is happening and if there is a way around it?

I had a go at installing Itunes under Wine but that was an epic fail (though I would much rather avoid using itunes anyway if possible).

Cheers,

Lee.