Being able to articulate why you don't like something is really instructive. Knowing why you prefer something, in specific terms, is really handy. I think they are both essential for being able to give solid critiques of your own work and of others when asked. At the end of the day, we all are drawn to what we like and push away or avoid what we don't but as you said, the latter gets you out of your comfort zone and can teach you more about what you do like and why. Mike Matessi has an exercise for developing one's taste where you create a "Like" board and a "Hate" board and you have to be able to justify selections in both per your own taste but in line with the tools of visual art: line, value, colour relationships, edge, shape, texture, composition/design, and narrative etc as best as you can. Something I noticed as you were drawing through Jinx, and got to the boots. You mentioned the "Joker" and a sense of being undone. Absolutely, but also look at the shapes of the hair and the hanging uppers of the boots, along with the striped pants. All I could think was that it evokes "jester".