Fuck me, what century do you live in

Unless you particularly want iTunes, avoid it. I use a small app called "YamiPod", it doesnt need to be installed, and works fine for what I need, just drag and drop files onto the application, and it sorts out the small indexing file on the ipod.

iTunes is the correct way to do it, but its big, bloated and intrusive so if all you wanna do is put your current colletion on your ipod, use yami.