zapper,

I recommend iTunes only for people who have an iPod; it's the easiest way to update the firmware. However, iTunes is too bloated and too limited for it to be of much value for anything else.

There are very good programs for managing your playlists and transferring files to/from your computer. There are at least two free programs that are cross-platform (you can store the program on your pod and then run it on any computer - Mac, PC, Linux - to transfer files). A Google search should make them easy to find. (I've not yet found a totally free program to transfer videos, but plenty to transfer songs).