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Originally Posted by MontanaXVI
Not to turn this into a whole "what to use" thread, but above mentions of iTunes because you have to make me shudder. I dumped iTunes a long time ago and use Red Chair Softwares Anapod explorer. You can add and remove tunes from your iPod with the program.
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... or you can completely dump the iPod firmware (if the iPod isn't significantly newer, i.e. with firmware encryption), and
Rockbox it so that it behaves like an ordinary external device.