Predictability and repetition. To illustrate the first, here's what iTunes genius came up with when I used U2's "Sunday Bloody Sunday" as a seed track. This is using an iTunes library with 8404 tracks, by the way, nearly all of which should be indexed iTunes genius since they're music that's generally available--so there shouldn't be any lack of options for iTunes to choose from.)
This playlist at least does a good job with diversity of genre and decade--there's 60s, 70s, 80s, 90s and 00s music all represented, and while most of it is alternative rock, there is some classic as well (Dylan and Simon & Garfunkel.) However, my issue with this selection of songs is that it's a lot of pretty predictable, burnt selections. With only a few exceptions, most of these songs you could still hear these songs on good ol' FM radio.
Of course, "Sunday Bloody Sunday" was a pretty big song for U2, so let's try a more obscure track from the same album.
This time, genius does a better job with predictability. Instead of picking the biggest hit from the album, it seems to have gone with the second or third biggest hits (which, in a sense, is a bit predictable, so perhaps I should have said that iTunes did a better job of not picking burnt songs.)
The other problem I have with these two playlists is lack of artist variety. This may not be true for all iTunes users, but if I pick a U2 song, that doesn't mean I want to a playlist of all U2 songs. In fact, I would prefer that in a playlist of 25 songs, there be no artist repetition at all. In the first playlist, there are 13 unique artists, and in the second only 10. To me, that feels like a lack of imagination. Especially since in my library there are many artists that I think relate to U2 in style, genre and era.
There are some things I really like about the genius feature, like it's convenience and the idea of quickly generating a playlist of related tracks, but I wish it allowed a bit more granularity in its controls. I'm thinking of sliders (or even checkboxes) that would allow one to adjust the variety of artists and the relative obscurity of the tracks it plays.

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