It’s just branding, though. This piece of paper is only linked to that athlete because I said so.
Well, for one thing it’s not necessarily always right and fair.
And there are plenty of times when a painting of trees has other meaning that makes it more valuable - often because of historical significance. It might be the first time trees were seen in that particular way, or using a particular medium, or in combination with other elements.
The analogy kind of runs out re: trees, because nobody’s all that fascinated with them by and large. Now, talk about paintings of people and there are all sorts of examples where historical significance or the artist’s approach is what makes a piece valuable. People’s way of seeing other people has changed vastly in the last couple thousand years, and it’s represented in artwork.
That’s the confusing thing about museums - often the aesthetics of the art are specific to the era in which it was created. It’s about context, as seen through the curator’s eyes.
Museums in small towns can be horrible - I’ve seen plenty of godawful crappy drawings by famous artists hanging in prominent spots in little museums. They may be historically significant, but damn, they’re still lousy drawings. I just shake my head.
Now, in terms of learning to discern small differences that make one piece “better” than another (and by “better” I’m saying that a roomful of critics would reach a consensus) – that’s your question, right?
Well, my question for you is – how many books are allowed to be in the library? Is it necessary to rank them all by merit? Is it even possible to rank them all by merit? Isn’t there room in the world for Stephen King and William Shakespeare?
You want me to explain how Sotheby’s gets those prices for art? Explain how they get those prices for anything! It’s the buyer’s perception, and the history of the goods in the marketplace. And the fickle hand of fate 
Now------ is there a point to art school? Is there anything that can be learned/taught? YES. There’s visual grammar - composition, contrast, texture, hue, shading, etc etc etc. There’s putting your drawings on the wall when you’ve all had the same assignment & looking at how other people solved the visual problem at hand.
Art school critiques aren’t about “good/bad” judgments – instead the other students and the teacher reflect back on the visual experience they are having. “My eye goes right off the page at that strong line.” And “My eye dances through this middle section and is intrigued.” That kind of thing. The artist offers something and other people reflect their experience of what’s been offered. And then the artist can judge whether they reached their goals.
Yeah, it takes a long time 
But you know what - if you get into the habit of looking at good art, you will recognize its sensibility. You’ll notice, subconsciously perhaps, that it’s rich in content – that it has internal logic, that your eye is entertained, that you have a feeling of life taking place. That’s a beginning. That’s fine.
Those critics in a room, trying to judge the merits of one painting versus another, they’re going to be people who’ve spent time critiquing and training their eyes. They’re going to have an ability to see far more than most people.
And sometimes they’ll be wrong 