There are AppleScripts available at Doug's Apple Scripts (www.malcolmadams.com/itunes/index.php) that let you copy the information iTunes doesn't copy when you sync manually (play count, ratings, etc.). Just look under iPod at the link above.
by feaverthe on Mar 05, 04 | 11:23 pm
Watch out for the playcount manual update script, it appends the playcount instead of just adding new plays and will artificially inflate your counts.
by dfbills on Mar 05, 04 | 11:30 pm
When using auto-sync, does it reset your play counts when you connect/sync?
I believe you need to be using auto-sync.