I think the crux of the issue is, the separation of HTML from css came from an era when we were styling documents, nowadays we're increasingly styling webapps.
For me personally, I've rarely had a design to implement that didn't require a bunch of scaffolding html to conform to the design, css alone was never enough. But that means for all but the most trivial of changes you will need to touch the html and the css.
So the question becomes, is it worth maintaining that separation?
My experience has been that most sites get built, get signed off on, run for some number of years before the site get redesigned and rebuilt, we're rarely making changes to a site that are just simple like the colour of something, all that was decided during development, most of it was signed off on during the design phase even.
So I think that's the angle Tailwind fans take, if the point of separating css from html is to allow for easy changes to the design, but those changes are either never required or can't be achieved via css alone, what's the point? Better to go inline because the development process is quicker and easier.