Latest iPod Configuration -- Any New Hope?

I know there are several threads on the pieces of this question, but I hope this will be a convenient all in one place update for iPod users who really care about the sound.

I was an early adopter for iPod with great hopes for portable, audiophile sound. I know they are fine for convenience, working out blah blah blah, but that was not my main goal. Rather I wanted truly portable and truly high end sound for traveling. And even 20 or 30 uncompressed CDs would be wonderful and -- maybe Im weird - but more than enough for most plane flights!

In the end, I got frustrated and kept hitting dead ends even with the so called experts, so at this point, I have two iPods, several sets of headphones, some noise cancellation headphones, one of the original top of the line Headroom portable amps, circa 1996 with D Cell outboard battery pack, a 9V battery powered Grado headphone amp, and expensive custom earpieces gathering dust in my drawers.

I have tried the Apple lossless scheme and for me, it is unacceptable, not to mention the devious tricks which apparently limit the number of times the files can be copied.

Maybe some of you have cracked the code, but I have had nothing but problems trying to easily "tag" uncompressed files.

In addition, it seems WAV files drain the battery life and cause brief skips in the operation of the hard drive.

Taking my iPod for the first time for months today on my motorcycle, I was reminded that the Etymotics high end headphones DO NOT play well with the wimpy internal amp of the iPod.

I was so disappointed, that I thought I should somehow velcro the Grado amp into my bike jacket or something, but aside from the geeky complexity of this there is no line level out?!

You get the idea...

Dont get me wrong, its a great little gadget for casual listening.

But WHY isnt it so so so so so so much better?!?!?!?!?

Or have I missed something?

Thank you.