That's the other thing, tools are a really poor shortcut to competency and in practice just reflect the same level of mastery that caused the initial headache except with a different set of tools.
This isn't pure. Some things are genuinely less insane than others.
As an analogy, higher quality brushes, paint and canvases will make you a better painter but buying new brushes isn't going to be part of becoming the next Monet. Consumption isn't going to get you there.
The real competency as you point out, come at higher level coherency, which frankly takes about 5-10 years to get any good at. It's a cognitive mastery that's mostly independent of tools.
People want to seek out better tools as a proxy for the hard earned talent. It might get you further but at some point, knowing what you're doing is the only way to go.
It sucks. It's hard. It's frustrating. It's always changing and it's also unavoidable.
It hadn't occurred to me that people might be learning Tailwind as if it's a replacement for having to learn or understand CSS. If you treat it that way then you're bound to have a bad time, much like people who treat git as a series of commands to be memorised without any understanding of git's underlying data model.
I'll also admit that I've only ever used Tailwind on small-to-medium sized solo projects, so I don't know how it would hold up on a big team. But then the CSS has been an agonising, unmaintainable mess on every big collaborative project I've ever worked on even without Tailwind, so what is there to lose?