Leave the moderating to the moderators, kids.
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Managed to reduce my iTunes from 12.07GB to 7.82GB by deleting all the songs that I don't listen to/can't be located and by converting all the m4a files to mp3. Took ages to do it, buuuuuut it's worth it now to see how many songs I can fit on my poor little iPod<3edit: 738 songs can fit on my iPod now, and I've still got space for maybe 30 more the pain of deciding what should go on it is now non existent because I had to think about what else I could put on to fill the space xD