iPod touch rules (coupled with a Windows Mobile phone running WiFiRouter = anywhere internet access). Jailbreak it and it's even better. Alot of people use their mp3 player for just mp3's but it can be an entertaining little device as well. Tons of games, ssh, remote desktop connection, NES/SNES/MAME/Geneis emulators, etc. Good times. Now if only the battery lasted more than 2 hours while playing games :-P.
You can use a program called EphPod found at
http://www.ephpod.com/ to get music on/off your iPod (supports all versions of iPods now, accroding to the site). For video, apparently, you can use Winamp with a plugin called ml_ipod.
I used EphPod on an old old ipod but not on my touch yet and have never tried the Winamp video transfer method, but figured I'd share the info I have found.