Tailwind aggressively speeds up development time of components by allowing me to stay in the same cobtext when styling things. The brevity of class names also dramatically shortens the time spent writing styles. While working on the projects I'd setup with Tailwind, I felt far more productive.
However, those were new projects. After completing them and needing to go back and modify or maintain them, the experience has been horrible. The resulting style declarations (as class names) are completely unreadable and unmaintainable. I've tried organizing them and splitting class names onto multiple lines, but it has only cluttered things.
In my experience, Tailwind (and similar projects) produce styles that are effectively read only. They are superb when writing a new component and styling things from scratch, but maintenance is nonexistent.
Because of this, I've now switched to using a CSS-in-JS solution to gain the benefits of in-context styling and still have the ability to write CSS declarations in a structured and maintainable way.