get a zune 1 30gb for $99. woot has them often or i'm sure you can always get them on eBay for about the same price. the firmware was updated to the same firmware as the zune 2 and its less than half the price.
the zune software is slightly slow and you have to use it to sync, but I liked it after a while. a side note...there is an incompatibility with the zune software and some adobe products like illustrator.
if I travelled alot and I wanted wifi internet I'd probably look into a PSP. How much storage can you get on that and how much would it cost altogether?
Well I only travel to work and back. I work 20 days on up in a camp(Oilsands), and 8 days off back home. I have my laptop on camp so im thinking the wifi isn't really needed there, but i dont wanna really regret not having it anywhere else...
god damnit zune why cant you have wifi