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you can get your music off of your old iPod by browsing it as an external hard drive. the files will be named something like "A3KEF.mp3" and placed in random folders, but all the tags should be intact. in Windows you can search for "A word or phrase in the file" on the iPod drive, so type in the album or artist name and you should find the correct files.
most of my music is tagged and organized but iTunes Cover Flow always has problems. it separates compilations into a bunch of different "albums" even though the files are all in the same folder with the same album tag. to solve this i have to enter a new tag, "Album Artist," for each comp ... or check the "Part of a Compilation" box. This is very time-consuming given the size of my collection, and even when i fix it, the covers are still separated on my iPod.
i've given up on Cover Flow, and since iTunes takes 2 minutes to load i only use it to transfer music.
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