I have bee using iTunes since it was first presented in 2001. It's really one of the most useful peaces of software I have on my machine. I enjoy using it immensely. But on the other hand, it has quite a significant drawback cuz it's not able to transfer files between portable devices, which is quite bad to my mind, since I don't wanna limit myself to a single iPhone or whatever.
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Yet at the same time iTunes only has very limited support for the types of Music/Video files it will play.
It really is a pain having to transcode Music/Video files so they can be played in iTunes.