Just a comment on the nano-bit: Since you have a flash-mp3 player you don't have to worry about file-sizes which in case of harddrive-dittos have bearing since large files consume battery-power because of need to continuously swap data between ram and drive. Being an audiophile I think you should go for Apple Lossless (ALAC) instead of AAC. ALAC meaning large files only 20-30% (I think) smaller than the original wavs. Once you've found a way to get all your music into tagged flacs you can do the conversion to ALACs retaining all the tag-info.
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