Boxer, do you use Winamp to sync your iPod then?
Yep, works fine: As I say, mine is a mirror image of the audio on my hard drive, right down to the playlists.
Video, I load separately, I don't use winamp for video and, if I'm staying away, I generally load some TV programmes that I want to catch up with.
As I'd started it a long time ago, I also have a complete back up on DVD's, kept at a separate location, so I'm pretty well covered all round.
The album cover feature on both Winamp and itunes, comes up with so many wrong covers and missing covers, I don't think it's worth having(Or maybe it's my taste in music!).