iTunes on Mac not updating play counts from synced devices

At one time there was an option, I believe, where iTunes on Mac would count plays and dates of songs on synced devices. Is this correct? It no longer seems to work. Is this a settings issue or a change in capabilities?

What I am trying to accomplish is a playlist kept on Mac that accounts for plays on the synced device so that when I sync again with the same settings, the playlist changes. More specifically, a Mac playlist of highly rated songs that is too large for the iOS device, so it is filtered by play counts or last played dates including those on the iOS device.