Ok I have that on my todo list and will report back. In the meantime, now my iPod has synched Ok I'm trying the same thing with my friends new iPod and so far I've come up against a few hitches. I tried the same approach i.e. a few playlists at a time, eject and check iPod, then do some more. I started by doing a restore followed by an initialisation in MC before synching the first playlist. This is what I found:
Sync 1 - MC reported transfer failed (1 file) and I could see that the progress indicator was saying that it was converting a file. I found this to be a bit strange since I only had MP3's in the playlist. After acknowledging the message it carried on transferring. Unfortunately part way through the transfer the iPod ejected itself (faulty iPod?) and this caused my whole PC to lock up. I couldn't even get task manager up so I removed the iPod from the dock and pressed the reset button on my PC. The iPod seemed OK as many of the artists in the playlist were shown but the playlist itself was not shown.
Sync 2 - After sync 1 I decided to play it safe and initialise again. Then I synched a smaller playlist. Again MC reported a failed transfer and showed that it was converting a file (different one this time) that is already an MP3. I OK'd the message and this time the sync continued to the end. At the end it reported the file path of the failed file and I confirmed that there is no reason for MC to try and convert it. I immediately resynched and MC transfered just one more file i.e. the previously failed one, proving that it really didn't need converting.
Sync 3&4 - A few more playlists and all successfull.
Sync5 - in progress. Sync 6 will be the playlist that I did first time when the iPod ejected itself and if this is successful sync 7 will be the biggest one (5K tracks).
I'll keep you posted. Hope this is useful.