Wow, alot to parse here.
I typically write all my projects in custom SCSS using my own bespoke structure that allows me to keep things as DRY as possible while maintaining a common structure across projects. I also have some utility classes that I use often (similar to bootcrap, but more concise).
I used Tailwind for one project and, while I liked some of the advances they made for handling svg icons, I still prefer using my own bespoke SCSS.
Tailwind 2.0 is actually not that bad, and one advantage is that you can handle all your responsiveness directly in your HTML, rather than having to slap a bunch of media queries and constantly reference between template and style sheets.
Just my 2 cents, but I'd agree for much of what you described. I also don't understand why developers hate CSS. I think it's pretty incredible, and while it has its quirks, Javascript has just as many.