In the meantime, we went cycling today, in the heat and humidity. I wore my black bikini top, bike shorts, with a white technical shirt with built-in 30 UPF, that I took off when it was overcast. This outfit garnered a lot fewer weird looks than I would have expected. And a lot of the women looked like they were thinking what a good idea wish I'd thought to do that, not, you slut, which is what I was worried about.
I got the 40 gig iPod, and after much screaming, got the installation right. I'm thinking the apple lossless may be a viable way to switch from CDs to a smaller format, but because there's a level change, it's hard to A/B it on the stereo, so I'll let you know if I come up with a definitive answer.