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Oneironaut

 
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Member Since: Feb 23, 2009
Posts: 1,320
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Whew, what a post! I could barely get through it because it sounds like monkeywhistle is making it way more complicated than it needs to be. I think your first mistake was getting thrown by the Summary tab's Options list that has "Manually manage music and videos". I would just ignore that and leave it unchecked. I know this option seems like it gives you more control, but it's really a pain compared to just having it automatically sync all changes made to playlists, library, etc.

For instance, let's say you just added ten new songs to your library and deleted five. If you DON'T opt to manually manage music, iTunes will automatically sync the ten new songs to your device and delete the five missing ones without any action on your part. With the manually manage option checked, you'd have to drag the ten new songs to the device or they won't get synced, and you have to manually remove the five deleted songs.

I would just leave manual managing off and simply choose which playlists, albums, etc you want to sync. It's really not that hard at all. Though I think some of these options could be better explained within the interface.
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