I do not know much about CSS but Tailwind was very straightforward, and through it I got to learn things in CSS which weren't made obvious before. It's funny that you use the terms "tedious mess" because that's exactly how I feel about CSS without it. Handling screen sizes, print, colors, and simple layouts.. all that seems way too annoying to do in pure CSS to my non-frontend-dev mind, and trivial to do with Tailwind.