I'm in a similar position to you and after getting throughly fed up with itunes (10,000 lossless aac files later) and trying out flac files (decoded natively on the sb2/3) I have adopted jriver media centre which will let you rip to flac but automatically recognises an attached ipod - when you drag you flac files to the pod it automatically trancode them on the fly to mp3 just for the ipod - its painless and means you dont have to have duplicate files being maintained. Media Centre is not free but its pretty cheap - has tons of other features including excellent tagging facilities (tag from filename - move file based on tag etc) and you can try it out free.
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