I use iTunes to import my music, then transfer to the iPod. It's easy. Basically setup so a child could use it.
I have over 400 CDs (and 2 hard drives full of music from a DJ buddy and another buddy that's a bar owner), so I imported all of them onto my NAS drive. Then, I just use iTues to skim through and add/remove music.
Get Electrical Connections setup for it. I have the old version that requires a separate wireless controller, but I like being able to see what is playing, coming up next etc.