Not to muddy the waters further (pun intended!), but the genre designation of "lo-fi" is really a misnomer if we are going to translate to audio gear. As I understand modern "lo-fi", it is more about rejection of uber-mastering, like auto-tune, extensive overdubbing, etc., in favor of more organic recording principles, like simpler gear, fewer takes, etc. Sometimes poverty is a factor, sometimes not. I don't think either of these approaches is superior, and I have enjoyed music from both, even on plankton-rich setups.
When I think about the initial reference to sky blue sky, an album I love, I have never thought that it was undeserving of the HD800, even from CD. I had the same general reaction to most of the albums/artists that were bantered about. Luis is right, "lofi doesn't mean low quality sound." There are shitty recordings on great studio gear, and great recordings on shitty gear. Also, sometimes the desired effect simply calls for lower tech production gear, even if one is later listening on high-fidelity headphones. Take Neutral Milk Hotel's In the Aeroplane Over the Sea as an example: Jeff Mangum's vocals on the title trackwhole album are meant to sound sad and kind of spooky, but on my HD800 he sounds downright haunting.
