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Itunes

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I can honestly say I've never had an issue in the last four years with iTunes. I don't really do anything out of the ordinary with it, but I doubt that's the issue given the nature of the specific complaint in the OP.
 
Machines will never choose the music I want to hear. They don't have the ability. If I want a playlist, I make a playlist. I also don't want anything "synced" aside from a small selection of documents I use in several areas. Again, I manually add what I need, and it gets duplicated across devices.

I have the option to drag and drop music manually to my iTunes, and I have the options for the most powerful playlists you can create in iTunes. There's no downside, and the other devices I'm limited to basically drag and drop and vastly inferior playlists.
 
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