I use apple lossless and yes you should use it vs. lossy. But the real bump-up in quality then comes from bypassing the headphone amp using a line-out cable (ipod or nano only); there you can either provide your own portable amp > headphone combo-- or line into your stereo.
For me, using apple lossless on a 5g ipod, through SIK Ram Din portable line out cable to Headroom Total Airhead portable headphone amp to either my Etymotic ER4S, or even better sounding my Grado 225s; IMO this sounds pretty good, and is as good as portable audio comes if you have not tried it.
A 30g Ipod should hold approx. 75 lossless cds, so it sure beats carrying around a PCDP and 20 CDs for your travel audio.
For me, using apple lossless on a 5g ipod, through SIK Ram Din portable line out cable to Headroom Total Airhead portable headphone amp to either my Etymotic ER4S, or even better sounding my Grado 225s; IMO this sounds pretty good, and is as good as portable audio comes if you have not tried it.
A 30g Ipod should hold approx. 75 lossless cds, so it sure beats carrying around a PCDP and 20 CDs for your travel audio.