I'm also looking to upgrade my portable listening rig. I have a 3rd Gen IPod that I've had now for about 2 years and I've been pretty satisfied so far. Anyway, I haven't really kept up all too much on this stuff since I've had my IPod... anyone have some suggestions? The IRiver looks cool but I have a PSP I can play video on so a player that plays strictly music would be ideal.
if you are just wanting an upgrade in sound, how about an upgrade in headphones? maybe some grado's? ety's?
I have a pair of shures that don't really need upgrading so Im good in that department.
If you are just looking for hotel playback type stuff, the sonic impact t-amp with the carboard speakers doesn't sound too bad.
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A cowon player (XL5 is the model# i think) has been getting a lot of attention over at head-fi.
Build a PIMETA, CMoy, etc. and buy the best pair of Senns your budget allows.