Ack! I have the same symptoms as well!
I just purchased a 4GB Nano am trying out MC 1.1.186. My iPod came with Updater 2006-01-10, v1.1.
Details: I have have two playlists, one with 156 iTunes (m4p) titles and one with 414 rips (flac). I am set up to sync both these to the iPod. The flac files are set to be converted to mp3s upon sync.
I think perhaps this might be related to the size of the playlists. I made a pair of test playlists, one with 2 m4p files and one with 2 flac files. This pair of playlists syncs OK.
I also tried to sync only the m4p files and this seems to work OK.
The problem with the flac files is that it is hard to try a lot of combinations because it takes a couple-to-several hours to convert/sync, even with my AMD 64 X2 3800+.
It isn't clear that it always does it either. But it happens often enough to be pretty much unusable.
Note this is with careful disconnects and making sure I'm not running iTunes + MC at the same time, etc.
I also recall seeing a post about "waiting a while" after the sync is done. If the "a while" gets longer as the sync list gets longer, perhaps we are disconnecting (ejecting) too soon? Certainly, once the sync is done, I don't see anything suggesting it is still doing anything and is unsafe to eject.
The gotcha is that you can't download 2006-03-23 (1.1.1) from the Apple web site anymore. If you search the downloads, you can find the download page, but when you download the file, you actually get 6-28, the very one Sterling warns against!
I also wonder what happens if you run out of space on the iPod while syncing. It obviously is going to be hard to estimate how much space the converted flacs are going to take up.
So, I'm stuck between a rock and a hard place. 1.1 doesn't appear to work well, and Sterling reports 1.2 doesn't work well, and I can't get 1.1.1.
I just wiped my iPod am going to start a from-scratch sync and leave it running over night. This should let it finish and sit for quite a while. I'll report what happens.
I really like the idea of having MC being able to handle all the content -- and the ability to have my rips in lossless format and converted on sync. But all these cool features aren't very helpful if it doesn't work reliably.
Any thoughts/suggestions would be appreciated.
Thanks,
-john