Again, at least part of the core issues I have is coming in to other projects where each person thinks in a 'different way'. And almost all of them are simply copy/pasting loads of tailwind extended strings of stuff, then semi randomly tweaking until something looks 'ok', then moving on.

> scan disparately located CSS files anyway

usually, I encounter CSS in one of two ways:

1. a main base css file or set of files (from a framework, maybe), and then an override css file. Single override file can get hairy to look through, admittedly, but it's typically in one spot. I rarely come across projects with dozens of standalone css files.

2. 'style-in-components' - primarily in vue, because vue sfc encourages scoped styling - structure, code, style in a single file. Whether that's bootstrap styling ('btn btn-primary', etc) or tailwind doesn't make too much of a difference.

Where I've hit more maintenance issues is coming in to projects with tailwind in say, react or vue - with the 'style in components' - is that "text-xs px-1 rounded-sm bg-gray-200 inline-block text-gray-600 mb-1" repeated across multiple components, is harder to find when I want to replicate something vs just "class='tooltip'"

Of course, we're all doing it wrong, and if we all just 'think different' all the time, and spend loads of time rewriting "wrong" stuff from other people - things will be just fine. But the world I live in, and the world I see a lot of people in - is not greenfield, but brownfield, and we have to live with the decisions others made. Tailwind does not make my life any easier that way, and generally introduces more cognitive overhead earlier in a project when it comes to visual stuff.