really...256 is crappy? you one of those people that can hear the difference between a $3k wire and a regular radio shack one? you buy Grados, Denons, Beyers, AT, Denons, or whatever flavor du jour cans? do you use phrases like PRaT, toe-tapping, warmth, soundstage etc... in your daily vocabulary?
a 256 rip from a
quality recording should sound exemplary, a 192 rip should sound pretty good, a 128-160 rip should sound decent.
here's the catch, we are all assuming these artists are using top notch instruments, badass recording hardware and superb sound engineers. i'm going to assume that the recording industry, like every industry there is, can't use top shelf gear for everyone. just ain't possible.
of course some independant ones have their own gear so i can't attest to the quality coming from them.
so chances are your pet artist probably strolled into a Warner/Sony/Universal studio, strummed an ok guitar, that was connected to a decent amp, which was recorded in an so-so sound room, armed with last years gear and proofed by some dude that produces mediocre work. then somewhere along the analog-to-digital process the music probably lost some of that dynamic warmness that LP lovers moan about.
if a 256 rip from that sounds "horrible" to the golden eared audiogeeks out there, then chances are the lossless rip isn't going to turn your tunes into sunshine and rainbows.
Are to any plans to actually make iTunes Plus songs have actual CD-quality, of 320 kbps? I recently rebuilt many of my playlists with much higher quality cuts of the same songs, and, with a good pair of headphones, the improved quality is amazing. It's amazing all the things that you miss when stuck with crappy 128/256 kbps.