using 11.0.234 here and I have two problems with the 'sync data' option.
The first one you already know of: auto sync won't sync data.
The second one is more serious since it screwed most of my playcount. Here's what happens. When you retag a file that's been played at least once in MC and then sync with the iPod, the playcount is incremented on the iPod. After that, as long as you don't close MC each time it is 'syncing portable info with MC', the playcount in MC is in turn incremented by the playcount on the iPod. Here's an example:
Track X played twice in MC and retagged (let's say you change the rating)
Track y played once in MC and retagged
Track Z played three times in MC but not retagged
After a manual sync here's what you have on the iPod:
Track X, playcount = 2
Track Y, playcount = 1
Track Z, playcount = 0
If you sync manually again, here's what you have in MC:
Track X, playcount = 4
Track Y, playcount = 2
Track Z, playcount = 3
Nothing changes on the iPod.
Retag track X again. Manual sync. Here's what you have next.
In MC:
Track X, playcount = 8
Track Y, playcount = 2
Track Z, playcount = 3
On the iPod:
X= 8
Y= 2
Z= 0
The playcount will keep increasing this way on each sync (actually, it seems you don't even need to sync: it appears to happen each time the 'syncing portable info to MC' message appears). If you close MC, run MC and sync, this won't happen again. But in the meantime, a track I played twice in MC and retagged twice, now shows that it's been played 48 times after just a few syncs...
Sorry for the long post, but I don't know how to better describe what's happening here.