> forget what name I had decided on

I think that's not the problem with CSS, but with how you approach design. If you treat your design process as editing a document, and just want to "Ctrl+B" to bold necessary parts, yes, I'm sure Tailwind's better. But, I can see how it could be a problem with maintenance and collaboration as there isn't an agreed upon design language or a document structure.

I understand that managing multiple files and going back and forth can be considered an overhead, but that's a componentization problem, not a problem with CSS per se, and you expect to recuperate your losses with the time you gained when finding and fixing bugs. Otherwise, there's no point in componentization. You'd have the same tradeoff when writing JavaScript code, for example.

You'd encounter the same set of problems the moment you start refactoring your styles into Tailwind components.