Yeah, good question. At a high level I think the best analogy is React: when I first saw it, I wasn't entirely sure about mixing in HTML with my Javascript. It seemed strange. Now that I've been using React for years, however, collocating these things seems like the obviously correct thing to do.
Tailwind is similar: instead of extracting styles out to a separated styled component or even a separate .scss file, you collocate them with the rest of your layout. When I read code using Tailwind it's easy for me to "see" how things will look in a similar way that I can "see" how a React component will function at run time.
More concretely, I think these three things were important for me:
1. There's a really solid design system underpinning the Tailwind utility classes. With styled-components you start from nothing, and with off-the-shelf component libraries (e.g. MUI) you get a design system that isn't quite as well thought out. Tailwind's classes just work together really well out of the box because the defaults are so sensible. I'm not a designer, so this is a really big win for me.
2. Components help prevent class soup. I suspect I wouldn't enjoy Tailwind quite so much if I were writing plain HTML, but for things which _do_ need to be reusable like button styles I'm still writing code that looks like `<Button>...</Button>`. Nothing really changes here from styled-components -> Tailwind other than how the styles are written; they're equally maintainable.
3. One-off snowflake UIs are really easy to implement, because you can just write your classes right then and there. I've never worked on a nontrivial web application where _everything_ fits cleanly into the design system, and going through the ceremony of creating a styled component just to add a little bit of additional spacing is a pain. It also sucks for maintainability because a name like "Spacer" doesn't tell me anything about the styles, so I need to context switch and jump to the definition. In contrast, seeing "mx-2" instantly tells me what's happening.
I do think Tailwind's something that benefits from first-hand experience, though.