Thanks for reporting, this is a regression, to be fixed as http://www.ventismedia.com/mantis/view.php?id=11275

This has already been raised (the need to sync play data (and tag changes) back to the Library prior to building sync list).

I am using MMW to sync unplayed podcast episodes to MMA. Currently if I play an episode in MMA then sync, the file is marked as played in MMW but is left on the sync list as if it is still unplayed. I then have to run another sync to have that episode deleted and the next episode copied to the device. I have also noticed that the same problem occurs with AutoPlaylists that use 'play count' or 'last played' as part of the criteria.

The net result of this is that every time I want to sync my device I have to run the sync process twice.

Could the sync process be changed slightly so that the sync list isn't created until after metadata is updated?