To me.. I will just rip to lossless, to prevent myself from losing out on any details But to be frank, if you want me to a/b it, I cant tell most of the time =( Some 320kbps and flac or alac simply sound similar, there is a definite difference, but I cant tell whether this difference implies song A is lossless or not, as it makes both of them unique, like comparing wav lossless against apple alac. but heck, just get the highest form of uncompressed audio and stop worrying is what I would say.. the difference might be small and might be only engraved onto your "sound" memory after time, but we are pursuing high quality audio, yes ? but for some music, there is certainly very audible SOUND QUALITY difference, and not mere different sounding, but SQ differences. Well, some of my friends claim that they can differentiate them easily, but oh well, it cant be helped, so why fret over it ?