I freely admit I waited until last to transfer the iPhone over. I knew from past experience that iTunes has little to no real library services or migration tools. Quite frankly, the iTunes application is a lump of coal in the otherwise jeweled Apple tiara.
All of my music is backed up on my NAS device...far more music than my 16 GB iPhone 3G will even hold. Of course, importing all of my music to the Macbook worked OK, especially since I did that over 1GB ethernet and not WiFi.
But, then there was the hard part. How do I transfer my "iPhone" playlist to the Macbook, so when I am forced by iTunes to wipe my iPhone and start over to sync it on the Mac, I can resync the music I want on the iPhone without having to go back and manually rebuild the playlist? I finally gave in and bought a third party tool which transfers playlists and other metadata.
What a smirch on Apple's reputation, that the company which revolutionized portable digital music has such a horrible gap in its library management tools.
So now I have the iPhone synced on the Macbook, with all of my playlists intact, thanks to a third party application. However I now have two and three copies of many songs again. Now I have to manually dedupe the library and hope I don't screw up the iPhone play list in the process. Oi.
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