Ultimately, it really is "a couple hours of thinking/configuring a linter vs. multiple layers of abstraction, complexity and dependencies added to the codebase."
Maybe I'm missing something (and be my guest if I do!) but there is an objectively better choice here.
I really dislike sass the way it's normally used. It was once a necessary hack, but it's mostly not useful anymore. Something that just concatenates your CSS @include on deployment would bring more value nowadays.
There's a default config, with only base rules, without the more opinionated ones. Then you configure/extend it as you would with almost any other tool. Isn't it the way most tools of this kind work?
Or am I missing something?
IMO, missing some rules is better than what most tools of this kind do, but something as plain and obvious as "did you enable debugging symbols on the development build?" should be there. And most people will blame the tool if it's missing.
As I see it, the problem was one of SASS code architecture. What do you mean then by "enable debugging symbols"? How does that solve the "chaotic file architecture" problem?
Tailwind is seeing steadily increasingly popularity (and the accompanying backlash) because it is straight forward and does not require something like stylelint to keep you from hurting yourself.