So this is how awesome technology (especially web 'cloud' services) are these days.
I now use drop.io as a place for friends to upload music to. I get an e-mail when new files are added. If I'm at work, I save files I'm interested in to my DropBox folder, which automatically syncs to my DropBox folder at home. Are you following me camera guy?
At home, I have Belvedere set up to automatically monitor mp3 files in my dropbox folder and add them to iTunes.
In iTunes, I have a 'smart playlist' of 'recently added' tracks, which those files get added to. When I plug my iPod in, it syncs that playlist automatically.
So when I'm out and about and want to hear new music, I check out my 'recently played' list and listen to new stuff.
That's wizard-level shit right there. Thanks to: http://drop.io