Lossless means lossless. It's identical to an AIFF file.
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You'll quickly run into problems with how your files are organized of the computer you're using to download to the iPods. It can be done, but multiple formats can get complicated. As a practical matter 40 hrs. of music is quite a large amount of music. Do you really gain that much from going to 85 hours? Couldn't the same be accomplished by simply updating/exchanging the music files on the iPod you want to listen to?