Hmm, alternatively, if you arent planning on playing lossless on the ipod (due to the size constraints), I would say a flac archive on your machine, with pmp_ipod transcoding to aac or mp3 on transfer would work out just fine.
Or what J_Darnley said.
Note however that apple lossless support is based on reverse engineering work that someone published into the public domain (lgpl?). So may or may not be feature complete.
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