This EXACT problem is occuring with me. I posted this in another topic: viewtopic.php?f=12&t=66283&p=342173#p342173
but it seems more appropriate here:
" I have an Ipod Touch 3rd generation using IOS 5.1.1. I am trying to sync with the latest MM version. I sync ONLY playlists made in MM. I do not have Itunes installed on this computer, but have the drivers via the "Copy Trans Drivers Installer" a user suggested.
It kind of works, but not really. If I only do a small subset of my playlists it seems to work, but when I do them all (5000 songs) It either
1) Force closes MM before the playlist associations occur. This means the songs are on my Ipod, but MM doesn't realize they are. or
2) If it makes it to the end some songs show up grayed out on IPOD. I am not sure if they are on Ipod or not.
This Ipod was Jailbroken and I reset it to "out of the box" via Itunes on another computer."
please help me.