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i think I turned my ipod into a generic storage device, put on rockbox, and just put stuff on myself. However, this might not quite be the setup you're looking for, because in the end I have to do everything myself...uploading, playlist creation, etc. Not sure what to tell you in regards to having a GUI similar to itunes to do it all, but this is working for me so far.
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If you're not questioning my sanity, I'm not trying hard enough
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