Links to scripts that can take an audio file and automatically upload it for you, and others that can find them in RSS feeds and automatically download them for you, put them on your iPod when you sync, and bling you’ve got the latest news/music/whatever with minimal hassle.
It’s still too difficult, but having minds like Adam’s and Dave Winer’s (through whose blog i found the link) on this make it more likely it’ll become much easier.