I also feel that algorithm based recommendation services are not going to be better than humans at least for a long time. Algorithms can recommend related stuff well(?) but that's not enough as our tastes keep changing and as you said they don't take risk.
I am thinking of building a radio like service where the playlist is curated by people listening to it. Do you think it's worth building? Any other inputs you'd like to add?
I shudder when I wind up listening to Kaskade because I started an Astral Projection station on Pandora. Last.fm was a bit better, but just not the same as AudioGalaxy of yore. Algorithms don't push barriers and take risk (or at least do either "properly"); it's the exact opposite of what they're trying to do.