I have the 40GB iPod with 5.4 days worth of music (1900 songs), the bulk of which are 320kbs VBR MP3's with some 128kbs and 256kbs MP3's as well as a few in Apple Lossless encoding, all of which uses only 12GB of capacity.
I primarily use it for air travel and I've found sound quality to be fine for that purpose. I use etymotic ER6 earphones (same idea as the Shure's) which work quite well for isolation on planes. Audiofranj is correct, you do hear body noises more clearly with earphones - the first time I ate an airplane pretzel with the etymotics in, I thought my head was exploding. However, I found the sound to be much better than Bose noise cancelling headphones supplied by American Airlines.
Ultimately, the question is what you are planning to use it for.
I primarily use it for air travel and I've found sound quality to be fine for that purpose. I use etymotic ER6 earphones (same idea as the Shure's) which work quite well for isolation on planes. Audiofranj is correct, you do hear body noises more clearly with earphones - the first time I ate an airplane pretzel with the etymotics in, I thought my head was exploding. However, I found the sound to be much better than Bose noise cancelling headphones supplied by American Airlines.
Ultimately, the question is what you are planning to use it for.