When I sync my iPod Classic 160GB to MusicBee, it will delete 150 songs (I counted them manually), and then re-add them. Because of this. it always takes 5-15 minutes to sync my iPod, even when I add one song to my collection. Also, it always says "syncronization failed", but songs and playlists are always correctly updated. When I first got MusicBee, I restored the iPod in iTunes, so the software is fresh.
I just did a test where I synchronized my iPod, and after it finished I synced it again. It deleted the 150 songs yet again!
Here are my iPod settings:
Edit: Disabling "Delete tracks that are not on the auto-sync list" doesn't stop the 150 tracks from being copied over.
Edit 2: With "Delete tracks that are not on the auto-sync list" disabled, those 150 tracks that are copied are not overwriting the old ones, but adding to the collection, and filling up my iPod even more. Enabling the option again deleted all the extra tracks.
Also, there are a couple songs that say "file missing". One of them I cannot find in my collection, and the other has a file name that doesn't match the song in my collection (it has a "_1" on the end of the file name). I rescanned my library, but it didn't fix this issue. This might be why I'm getting the "Synchronization Failed" message at the end.