SlimServer (which is the application that squeezeboxes use) dont require you to have the music library affiliated with any other program then slimserver itself. So you dont really need to use itunes or any other program.
EAC for burning if youre on a windows machine
MD didnt think they had good low level detail as well.
I think the low level detail on Colin's rig was great. The headphone sounds progressively worse with less powered amps
I have an older Kelty backpack for my laptop/school stuff.
Its super light and carries a shitload of stuff around. If you're going to carry a laptop around, I suggest padding the bottom with foam since the laptop compartment isint padded.