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Eliezer_Yudkowsky comments on How to Write Deep Characters - Less Wrong
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I have no "so bad it's good" gene, so I would usually stop reading such a work instantly, like a fanfic with multiple spelling errors in the first chapter. If I had to name a work I read all the way through, Lev Grossman, The Magicians. It's well-written along all other dimensions but I found the protagonists to be needlessly existential - the 'protagonists bored with everything' turned what could have been a great book into a merely good one. That is a literarily influenced SF&F story, of course.
So there's "moral ambiguity because questions are hard and author smartly doesn't want to impose pat solutions" and "author is bad at that and is doing a 'grittiness of the gaps' thing." I don't know if we draw the boundary in the same place.