I hypothesise that enduring musical masterpieces will possess an interesting objective property: despite apparent complexity, they will also exhibit high compressibility.
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I contend that a seminal point in human history must have occurred when the act of compressing sensory patterns became intrinsically satisfying in its own right. As brain complexity and consciousness led to greater sophistication in the sensory stream's interpretation and reward system, a multitude of compressible sensory inputs could became increasingly pleasurable.
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I speculate that when we appreciate music, a major influencing factor is the release of pleasure that comes from performing a surprisingly profound audio data compression. By this logic, one would anticipate the level of pleasure to scale with the mismatch between the apparent complexity initially perceived by our ears and the real simplicity subsequently resolved in our minds.

If you want to discuss this amongst yourselves, I've posted it to the subreddit.

To sum up, the modern economy is primarily composed of things and services available for money, ratcheting to allow fewer and fewer non-monetary costs. When things are available for money, anyone can acquire them; this dilutes the information about the self that can be contained in the ownership. Similarly, a major trend in the labor market is toward fungible skills that anyone can supply, reducing opportunities for virtuosity and positive information about the self through work. Everything is increasingly available for money, except, I will argue, a major thing we all want to buy that gives us the feeling of meaning: our own value and specialness.
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The mistake is to view hipsterdom as pure signaling. It invokes signaling, of course, but also the genuine, authentic search for value in genuineness and authenticity. The hipster is a person who is particularly alienated by the world of purely fungible culture. His music and books, his old "vintage" items, are more demanding, harder to find. But at the same time, he is made more interesting and valuable through what they demand from him.
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The fungibility of work, the reduction of demand for long-developed special skills, the impossibility of virtuosity in one's limited job, has made work less and less a source of reliable, positive information about the increasing value of the self - because it has ceased to truly improve people. But people still desire to work at what they love, and to improve themselves. The market will sell them the feeling of this, but will not commonly supply them with food in exchange for pursuing virtuosity.

Going off on my own tangent, humans have two contradictory desires. We want to feel like we're valuable people living good lives, which itself is a massive and difficult subject. A good place to start is the famous video, The surprising truth about what motivates us. The other thing we want is for life to be easy, but there is a trade-off between a good life and an easy life.

This conflict comes into clearer focus as more work is automated. Do you want a machine where you push a button and food comes out, or do you want the challenge and personal empowerment of growing and preparing food with your own hands? This was not an issue in preindustrial civilization, when work was done by slaves and peasants. The lower classes suffered, but not from existential angst, and the elite felt important because they were ruling actual humans. Now there is a growing class of people who have no political power but are served by machines.

If the tech system can pass through the bottleneck of resource exhaustion (I think it can, but that's another subject) we might emerge into a high-tech utopia/dystopia, in which it's easy to be comfortable but difficult to be happy. Social class will no longer be about power or even standard of living, but valuable activity. The upper class will hold the few important jobs that still require humans. The middle class will be hobbyists, practicing difficult skills that are not necessary for society. And the lower class will be content to consume entertainment.

A host of studies have found that people who are easily bored may also be at greater risk for depression, anxiety disorders, gambling addictions, eating disorders, aggression and other psychosocial issues. Boredom can also exacerbate existing mental illness. And, according to at least one 2010 study, people who are more easily bored are two-and-a-half times more likely to die of heart disease.

This raises the question, which cannot yet be answered except by guessing: what exactly makes different people more or less easily bored? Personally I'm so resistant to boredom that I sometimes fantasize about being in solitary confinement. My guess is that it's partly genetic, and the key environmental factor is how much free time you had in your first few years of life.