I'd rather make a "disk" of stuff I wanted to listen to and, as I'm leaving for work, grab it out of the front of the stereo and stick it in the car player while I'm driving to work then stick it in the front of my computer when I get to work. In any of those situations it would play hassle-free for as long as you cared to listen. And, for those folks who can't quit listening long enough to take a leak, they could have little memory-less iPod-like devices that you could plug your memory stick into when you went to the restroom or to the store room to get a new legal pad or whatever.
If you can abide the foggy grain of MP3, you could get a couple hundred tunes on a 1GB memory stick. If not, you could still put 60 or 70 losslessly compressed selections on one.
You could do the same thing with the little memory cards that they use in digital cameras and such, but why not use a format that is already built into every computer on earth?
I'm gonna go Google that and see if somebody's already doing it.