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It's a huge pain in the ass, and to make it worse it's different from device to device.
I have 5 different ipods between everyone in my family, and some you can drag songs, some you must create playlists, and some you can even drag a file from windows explorer onto the device in itunes & it'll copy.
For the iphone, I found it easiest to create a single playlist and then just drag whatever music I want into that. Then I just sync that one playlist.
Don't even get me started on the whole tethering business, either. I almost threw my phone against the wall when they disabled tethering in 3.1.
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