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Good points in general, and I can't speak for the wine part, but do want to be a bit pedantic about the whiskeys:

This is what wine/whisky differences are often about. Which stain is better? And why?

In the whiskey world, some differences are like this, but some really are more objective, like the dresser. Whether they're worth the extra money or not will be in the eye of the beholder, but it really does cost a lot more to produce a 12-year whiskey than a 4-year whiskey. Evaporation directly results in a loss of the angel's share, the capital costs of sitting on stock and warehousing it are significant, and staff have to continually monitor barrels (some things need to be taken earlier, you can't just rely on everything aging evenly). Some products also include finishing in other barrels (port or rum barreling has become pretty stylish). At the end of the day, I suppose someone could still prefer the cheaper 4-year, but I think it's pretty unlikely that you'd ever get that result with any consistency in a blind taste test.

I think your point holds up much better when comparing products that are objectively similar - does the price tag on a 9-Year Willett bottle make any sense? Not to me, which is why I don't buy it. Should 12-year bottles of Van Winkle branded things really run up into the four figures? Well, based on the couple times I've gotten to try them, I'd say that it absolutely doesn't make sense and that people like having those bottles on their shelves for status. But really, I will actually insist that most people who like bourbon will find a good 12-year single barrel more enjoyable than the mass market products from the same distillery.

A final note on signaling is that the hypothesis is doing too much work. I can't speak for others, but I don't host people very often and most of the people I host don't care about whiskey. I (probably overpaid) for a pricey Bardstown bottle recently - I don't think I even personally know anyone that has even heard of their products. Of course, I could have been convinced by marketing hype, I find that entirely plausible, but I can't really see the path to that being about signaling. Pay for a bottle that literally no one I know cares about, pour a dram at home with no guests, plop down and watch 1883. That seems... not about signaling. The most straightforward story is that it's actually good whiskey and there isn't a need to tack on any other motivation.

The obvious caveat applies that the article is about wine, not about bourbon - I'm mostly just assuming that the wine world behaves pretty similarly because it has all of the same underlying social dynamics and subjective impressions of flavors.

People signal to themselves, because you have a mental image of yourself in addition to others having a mental image of you. It may not be important for you to have others see you as wealthy, tasteful, refined, knowledgeable. It may still be important for you to see yourself as that. Why else would you test your own ability to identify whiskey? You're not immune to your own judgmental gaze.

I take your point about some whisky being orders of magnitude more time-consuming & expensive to produce, but that's part of my point.

Some products may advertise being "handmade!", and it takes 10x more time & effort to make them, but a machine actually does a better job of producing that product. People will still often pay more for the handmade product if that characteristic is used as a selling point, because brand recognition and perceived value are examples of how the human brain is easily hacked. People have clustered together notions of "quality" with the concept of "handmade" and reality is hard-pressed to convince them otherwise.

From the essay:

Or consider the famous Pepsi Challenge: Pepsi asked consumers to blind-taste-test Pepsi vs. Coke; most preferred Pepsi. But Coke maintains its high market share partly because when people are asked to nonblindly taste Coke and Pepsi (as they always do in the real world) people prefer Coke. Think of it as the brain combining two sources of input to make a final taste perception: the actual taste of the two sodas and a preconceived notion (probably based on great marketing) that Coke should taste better.

This is truly remarkable data. People come to expect Product A is better than Product B, and that expectation drives their experience...even when they actually think Product B is better when branding is not available.

On signaling: I'd say it's much more influential than we realize. Further, there is a sort of "self-signaling" at play. It's a deeper discussion, but I believe people's choices are a part of a narrative they are telling about themselves, and it contributes to their experienced happiness/satisfaction (Kahneman) as they traverse life. We all want to be the kind of character in the story who "appreciates good whisky" and "spends more for quality." We don't want to be the guy who has undiscriminating tastes.

the famous Pepsi Challenge:

Which is also a bit of a hoax/mirage. We know why Pepsi wins the Pepsi challenge: More Sweetness, less acidity. Those things also make Pepsi lose the Pepsi challenge if consumers are asked to grade drinking an entire can, particularly if it gets diluted by ice or gets slightly warmed over the course of drinking the can.