Alot of people say Mediamonkey or doubletwist, but those programs are horrible.
Disagree. MediaMonkey is a wonderful program. It is extremely powerful for tagging music, adding album art, building playlists, finding (and deleting) duplicate songs, and many other things.
And best of all, it will sync playlist and album art to the Pre properly! After initial setup, to sync your Pre all you have to do is plug it in and click sync (or set it to auto-sync upon connection).
I have the VZ PRE + and the older Itunes. Some of my songs would sync, others did not. The ones I bought on itunes recently worked, the older ones (06-09) didnt seem to work as a general rule. The artwork and songs appear, but when I "play" them there is no sound. What can I do?