Creator of Tailwind here — if you don’t want to go deep into JS tooling and really just care about spitting out a CSS file, it's a lot simpler to just use our CLI tool:
https://tailwindcss.com/docs/installation#using-tailwind-cli
It seems like Tailwind is popular enough now to support guides for more than just JS frameworks and Laravel :)
As I've seen many tutorials that were too complex to set up JIT with Tailwind, I thought it might be helpful to others as well who were having difficulty.
The next version of Rails will eliminate webpacker anyway, so I'll write for it