I have an experience that seems relevant.
I was assigned several chapters of the high-status The Landmark Thucydides: A Comprehensive Guide to the Peloponnesian War for a class, and fell in love with it, reading it over and over. I don't say status had nothing to do with it, for every effect has multiple causes (and every cause affects multiple things).
When the translator finished the similar-status and somewhat similar content The Landmark Herodotus: The Histories, I bought it and began reading it with the expectation I would find it stimulating on multiple levels. I found it very boring and randomly meandering, in the same way so many people say they find all of history, which I was finally able to relate to.
Perhaps I was sabotaged by high expectations that I only noticed not being met, but on the other hand I was primed to consider the book favorably and confirm that opinion.
Regarding your point 5., these are two of the earliest works of the art form, which is also a mark of something one is "supposed to like".
A meta-status theory would be that I validated my appreciation for Thucydides by disparaging Herodotus.
As for the Fugue, it was quite pleasant, though I thought the thirty seconds after 11:48 were silly.
I'm trying to like Beethoven's Great Fugue.
"This piece alone completely changed my life and how I perceive and appreciate music."
"Those that claim to love Beethoven but not this are fakers, frauds, wannabees, but most of all are people who are incapable of stopping everything for 10 minutes and reveling in absolute beauty, absolute perfection. Beethoven at his finest."
"This is the absolute peak of Beethoven."
"It's now my favorite piece by Beethoven."
These are some of the comments on the page. Articulate music lovers with excellent taste praise this piece to heaven. Plus, it was written by Beethoven.
It bores me.
The first two times I listened to it, it stirred no feelings in me except irritation and impatience for its end. I found it devoid of small-scale or large-scale structure or transitions, aimless, unharmonious, and deficient in melody, rhythm, and melodic or rhythmic coordination between the four parts, none of which I would care to hear by themselves (which is a key measure of the quality of a fugue).
Yet I feel strong pressure to like it. Liking Beethoven's Great Fugue marks you out as a music connoisseur.
I feel pressure to like other things as well. Bitter cabernets, Jackson Pollack paintings, James Joyce's Finnegan's Wake, the Love Song of J. Alfred Prufrock, the music of Arnold Schoenberg, and Burning Man. This is a pattern common to all arts. You recognize this pattern in a work when:
Here are some theories as to how a work becomes the darling of its medium or genre:
(Don't assume that the same theory is true for each of my examples. I think that the wine hierarchy and Alban Berg are nonsense, Jackson Pollack is an interesting one-trick pony, and Burning Man is great but would be even better with showers.)
I could keep listening to the Great Fugue, and see if I, too, come to love it in time. But what would that prove? Of course I would come to love it in time, if I listen to it over and over, earnestly trying to like it, convinced that by liking the Great Fugue I, too, would attain the heights of musical sophistication.
The fact that people come to like it over time is not even suggested by theory 1 - even supposing the music is simply so great as to be beyond the appreciation of the typical listener, why would listening to it repeatedly grant the listener this skill?
I have listened to it a few times, and am growing confused as to whether I like it or not. Why is this? Since when does one have to wonder whether one likes something or not?
I am afraid to keep listening to the Great Fugue. I would come to like it, whether it is great art or pretentious garbage. That wouldn't rule out any of my theories.
How can I figure out which it is before listening to it repeatedly?