So I experimented with loading songs onto the Watch. I loaded up 2GB of my favorite running songs, and am now waiting for my BT headphones. In the meantime I played it through a BT speaker I had lying around, and much to my disappointment even after I re-synced everything the play count and last played timestamp was not updated for the songs I played. This has always been key data for me and my playlists as well as just curiosity, going back to my first iPod in 2006. The plus side is that it does update the watch if you sync a smart playlist and it changes (and only updates the relevant songs, so it doesn't take all night). Has anyone actually had this update play counts or do I need to file a bug report?