Technical perfection vs. the element of surprise
I've had many experiences where I simply don't get what the artist is trying to do. In some cases, I've compared myself to the artist - trying to understand the appeal of the performance despite the fact that I don't particularly respect some aspect of that performance. In other cases, I have marvelled at the technical perfection of the performance yet wondered why it left me wanting to go do something - anything - else.
I really don't have a problem with technical perfection. I don't think that a performer has to be technically lacking to make an emotional connection with the audience. On the contrary, an unskilled performer loses the audience precisely because he/she stumbles over poor "vocabulary".
My own preference is for music in which it's clear that the performer is "stretching". Yes, that usually implies a technically imperfect performance. There's something about a flawless performance that leaves me cold. Perhaps it's the feeling that I didn't witness a "unique" performance - that the next flawless recital of the same piece of music would be indistinguishable from the last.
I grew up in a family of classically-trained musicians and learned, among other things, that one pianist's rendition of a piece could be subtly different from another pianist's rendition. However, I also noticed that I could identify the player - sight unseen - by how they played a particular piece of music.
Later on (before my teenage years), I fell in love with rock 'n roll for its rebelliousness (long since co-opted and commercialized) and unpredictability (long since squeezed out of existence by the likes of Pro-Tools, Auto-Tune, heavy compression, and sequencers). I still get a thrill from noticing the differences between one performance and the next and from being able to identify a performer from the nuances of their phrasing, note choice, etc.
Ironically, I find myself seeking out music that has a higher level of technicality because simpler musical forms are too "safe". But I'm still looking for the same thing that I've always sought in music: I'm looking to be surprised.