I'd recommend looking at
http://www.digmind.com/store/index_500.html , depending on your priorities. Several people I've known were looking at the iRiver because of drag-and-drop file loading (no iTunes type stuff).
The player I linked is ugly as sin, and a good inch longer and half inch wider than an iPod, but I bloody love it. I've used mine 6-10hrs daily for going on a year now with no problems, and it does everything I could want:
* 100GB (or smaller, if you don't need that much) for ~$330 (I bought and installed a 100GB HD myself and saved a lot) or a 40GB (upgradable) for $229
* truly 20hr+/- battery life on a single recharge
* plug-and-play, no copyright restrictions--upload to any friend's computer. It just acts as an external HD on a computer--no intermediating software.
* total control over how files are organised
* can record/enclde at up to 320kbps via a line in (optical included) and has a built-in voice recorder
* battery is user-replacable (no iPod type scam)
* upgradable firmware--already plays mp3, windows media, WAV, OGG, etc.