I might be reading a lot into this remark and mostly relying my own opinions here though.
But throughout the years I've been seeing how CSS is universally met with insane prejudice and expectation of it being "too complicated" or painful to learn, and Tailwind being praised as the solution while actually being much more verbose and obfuscated, and time after time leading to irrecoverable tech debt, utterly illegible markup, and complete dead ends whenever style needs any kind of refactoring.
Now that CSS is maturing and getting tons and tons of new features, Tailwind lags behind and keeps introducing more weird workarounds and hacks to be able to support all of it. The line in OPs comment is an example of it literally coming down to writing mutilated CSS selector statements directly to html attributes just to be able to do some of the stuff `:has()` enables, and creating horribly illegible markup and non-reusable styles in the process ...
Imho the original issue leading to "stylesheets are a pain" was never really CSS itself (at least since module 4 & custom props), but rather the top level management of tokens in a design system to not have to memorize colors and sizes etc -- Tailwind is simply collaterally fixing the right problem with the worst approach thinkable, but keeps being hailed as a holy grail by people who lack understanding of this.