1) Dewey's "experience">"looking" idea is a cool one, especially so because he leverages it into this anti-genre/medium argument where it logically follows that all mediums can be considered in the same way. Conceptually, I think it's super interesting; in practice, one of my hobby horses is that categories/labels are actually Good, and increase our enjoyment of the world... won't go into it here but I will say that Dewey's hypothetical artworld is so far removed from today that I think it's impossible to make accurate predictions about the pros and cons. Conceptually though super cool.
2) If you're interested in the whole Lincoln recognition thing you might (maybe!) find Charles S. Pierce's semiotics theories  interesting. Contemporary of Dewey, also pragmatist American philosopher, wrote essentially a masterpiece of semiotics in letters, correspondence that never got published. Throwing that out there.
3) I'm on board with Dewey's idea of experiences having a specific direction/order, but I wonder if you think it's true to say that these are "ideal orders" or "implied orders" more than "the correct order"? I'm thinking of how paintings, esp pre-20th C (though also some Abstract Expressionist stuff, other art), have a direction or flow to them that is implied by the artist... The viewer starts at a certain point that jumps out (and jumps out equally to most viewers) and then lines, color guides that viewer's eyes around the painting, following a path intended by the artist.
4) Fulfilling is a really good way to put what we look for out of art experiences, and a great way to qualify the argument that art is about enjoyment. I remember coming across his ideas in his Later Writings, vol. 4 and loving it (don't know the book; our library stacks just have a crazy 36-volume collection of Dewey's complete works; it's insane he wrote so much without modafinil... sort of joking sort of not. Can you imagine the Egyptians building pyramids pre-coffee?).
5) Hadn't read his narrative and living creature sections. Evpsych metaphor works well and is elegant even if I lack the science knowledge to verify its veracity.
6) Have you read his non-art crit pragmatist philosophy? I feel like people around here would be into it:
-He argues philosophy should be about improving resolving the issues of people and not the issues of philosophers. Also argues that his aim is to "intellectualize practice"
James is great too. James on Pragmatism: "a method of settling metaphysical disputes that otherwise might be interminable... The pragmatic method in such cases is to try to interpret each notion by tracing its respective practical consequences. What difference would it practically make to anyone of this notion rather than that notion were true?" (James, Pragmatism, 28)