Vinyl's coming back. At least up here it is... there are two record stores (as in honest to god records) in my wee little town here, and several outlets where you can buy turntables etc... some of it is used, some of it is "old-new", and some of it is just new. If you want compression but want it to be better, compress to 320Kbs cbr (er, constant bit rate) mp3 with the -q option at zero; you'll end up with bigger files but nowhere close to full audio, and they'll be pretty good... way better than FM radio, for example.
Besides, even with all that... the quality of the amp in the portable player, the dac in the portable player, and of course most of all of the headphones you're listening to have a much bigger effect on the quality of your listening experience.
Seriously Ash, it's a case of having a tradeoff... you can get something the size of your thumb and stuff hundreds or thousands of songs in it. That it's never any worse than an FM radio doesn't seem like a big drawback to me.