Biggest variable is how he ripped and stored the music. If it was MP-3 files and he can't hear the diff, then its 2 and/or 3. If he is playing lossless files then might be pretty good, although still could not rule out 2 and/or 3. AS far as 4 goes, a lot depends on how much downloading you want to do. As far as 1 goes, it is a relatively user friendly device that provides excellent portable music. It is pretty darn good at it, IMO. Of course, there ARE problems with the software and download interface, IMO, but most of it is probably a matter of my limited practice.
