There's another thread on this somewhere. . .

If you are using a Mac, the Missing Sync works well. It transfers all album art, playlists, etc., from iTunes to your Pre, and (unlike iTunes) puts the songs in visible directories where you can see them through the USB drive. The interface isn't quite as nifty (it doesn't tell you how much space you have, and compare that to the volume of files you've selected) but everything seems to work just fine.