Hey. I'm using ml_ipod 3.08p05 with Winamp 5.551 on Windows XP with a second generation iPod Touch running jailbroken 2.2.1 firmware. I have attempted to sync with Winamp but it gives me an error saying that the iTunesDB file could not be copied over and that I should delete some tracks o free up space. I have over four gigabytes of free space however. I decided to see if this was a problem with the plugin or my iPod. Because my iPod is jailbroken I have the ability to SSH in and drag and drop files. So I put the updated iTunesDB file from the location given in the log into my iPod. I fully shut down the iPod application (holding the home button until it quits) and then started it again. It worked perfectly. I thought that this may be of some interest to you. I hope this helps! Keep up the good work!
Adam