So you definitely have transferred the actual music files to the USB drive? Do they show up there on the USB drive (the actual files, which should be relatively large). I'm assuming the answer is yes, as the touch scanned and found the files. Odd that it is not playing apple lossless, but I have no experience with those files. You might want to convert your apple lossless to FLAC. The touch can play these natively. Dbpoweramp can convert all these files (losslessly) along with your tags and album art.
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