I have a collection of old Doctor Who shows that I've been adding to. The problem I'm having is when I add an older show it shows up as the most recently added, yes it does make since. When I sync the TV Shows I select the 10 Least Recent Unwatched option so I can watch them from the beginning. Naturally I'd like the added shows to sync if they are older than the ones I currently have on the iPhone, that would be older by the release date and not a older file on my Mac. I can make a smart playlist that does this but can't find a way to make it sync with the phone. I have just under 300 files so I'm trying to avoid editing the properties for each file manually. TIA.