I do not own and iPod but they are something of  craze in the rest of my unit. Most of the folks that own them are not techies just average soldier types and they love them. In the course of performing a music related task for one of these guys I found this :  JHymn and it's wealth of features (namely the stripping of DRM encryption from iTunes music).

     I have used professional commercially sold software that is less robust, less full featured, and with less documentation that JHymn comes with. It is Open Source freeware with no strings attached and was programmed by an anonymous developer simply because he doesn't like the limits placed on his property by DRM as he lays out in this interview.

Altruism on his part... I love that.