Some folks on #joiito turned me onto "streamripping". This is software that stores songs played on Internet radio stations as mp3's with meta data and everything. RadioLover is streamripping software for the Mac that lets you record multiple radio stations in parallel. You can drag and drop the songs into iTunes and sync to the iPod. The quality seems fine. I can listen to my favorite radio stations from all over the world when I'm walking in the park with my iPod. Is this illegal? It is SOOO useful it MUST be illegal. ;-p
UPDATE: For the record, I've just bought several albums on Apple's Music Store and Amazon that I didn't know about until I started messing around with RadioLover.