Same issue. Every time I connect my iPod (20GB) to my computer with WinAmp open, it immediately munges the iTunesDB file. I can use the .old file to get back to where I was, but I can not add any new songs or playlists to my iPod.
Any new fixes on this?
Also, where do you get to ipod tools to do a complete database repair? Not seeing it in WinAmp or on my iPod.