I'll offer a counter-anecdote and suggest this advice isn't necessarily ironclad. I've used the same pair of $20 headphones for decades (replacing them with the same model when they die), or else laptop/TV speakers. A couple of years ago I got $200 headphones included with a new phone purchase. The $200 headphones were amazing. I got to listen to all of my favorite music with a new perspective. But I still use the $20 ones on a daily basis because the $200 ones hurt my ears with prolonged usage. The $20 ones are fine. The nice ones didn't diminish my enjoyment of them at all. And every now and then I break out the $200 ones for a treat.
Just don't become a snob. I think people tie their identity to the expensive junk they purchase and develop a sense of ego around it, of being better than the peasants, and that's why they become unable to enjoy the "lesser" experience.
I think you point to the real problem: It's often not about taste or enjoyment but about using expensive things as a crutch for your feeble ego. Neatly expressed by the term "nouveau riche"
I think it's more to do with 'taste' as an indicator of social status. Not all things within the 'good taste' space or expensive. It's more about access to the secret club thinking, e.g. the secret hidden strip mall restaurant that has the best Bahn Mi.
Regarding audio, I have access to very decent headphones and also lower-grade studio monitors, as I've decided to make audio production a hobby of mine. Both of these are absolutely better than my cheaper in-ears for cycling and walking around outside. And sure, you also start to notice how different bluetooth boxes are also on a range of audio quality. And live music on a PA is a whole different ball game and not comparable to studio recordings entirely.
But that's fine. The in-ears are at a decent conjunction between audio quality and a price point I won't be hurt if I lose or break them. And some music from a janky box is better than no music from a janky box. At worst it will be funny how janky it is.
If I encounter something I like, I can ask what it is, break out the better equipment at home, probably sit down on the balcony with some tea or a drink and focus on the music and appreciate it for an hour or so while watching the magpies and crows in our back yard.
It's in fact even fun to me to dive into a song or an album like this to explore what you didn't hear on the other audio system. Sometimes there is an entire instrument you're missing on other systems.
The entire concept of "comfort food" and "poverty food" is about people excusing the enjoyment of "low class" stuff that is eminently enjoyable and shouldn't need justification.
You can learn tasting notes in wines, and how to identify wines that are well balanced with good tasting notes or an interesting character. You can appreciate all the care and expertise that went into that process and how it meshes with the "flavor pairing" guides and cheese that it was served with. You can then buy an entire case of $6 wine from that winery because that wine tastes exactly like Welches concord grape juice and when you were a kid you always expected wine to taste like tasty grape juice but make you drunk and have always been disappointed that wine doesn't taste like grape juice.
That wine was so good and it was $6 because snobs hate simple pleasures.
Don't be a snob. Good is not the inverse of simple, and complex is not inherently good.
Nobody can stop you from drinking boxed wine cut with gatorade. Nobody can stop you from enjoying boxed wine cut with gatorade.
If you find you can't enjoy the simple things, you don't need to "upgrade" or get more expensive stuff or keep up with the Jones's, you need therapy.
Just don't become a snob. I think people tie their identity to the expensive junk they purchase and develop a sense of ego around it, of being better than the peasants, and that's why they become unable to enjoy the "lesser" experience.