Expanding Radio's Playlist

I’ve been fascinated by the increasing popularity of radio stations that are using automated programming from a very large playlist of songs. Most of these are branded as Jack FM but some areas the stations go under other names.
I’d emailed Chris Anderson about this a while ago, because he’s Mr. Long Tail (see Is Jack FM the Long Tail of radio?) and because I’ve spent time in the music industry and helped in running an online radio station a few years ago. I’d love to see anything shake up the stagnation that plagues the terrestrial radio industry.
Chris naturally has some good thoughts here, and as more people notice the format, I’m curious to see if radio embraces any other tenets of the music experience we’re used to on our PCs and the Internet.
If you’re not familiar with the format, some of the best backgrounders are Time’s recent piece (as well as this piece from Time Canada) and an LA Times story which doesn’t show up in their archives, but has been reposted on So New York Online.