As a general note here:
I’m close to wrap up a new feature in Hugo that’s a new defer keyword in the templates, which allows you to defer a template block to be executed after all the rendering. I’m wrapping my head around some “live reload” technical issues as I write this, but my initial tests shows that the “Tailwind workflow” can be simplified, mostly in the sense that it should not be needed to have the hugo_stats.json file watched anymore, and shoud also give smoother rebuilds when you add new Tailwind classes to your templates (today that triggers 2 builds, 1 for the template change and then 1 for the CSS change).
That said, I have used Tailwind 3.x with Hugo extensively myself for the last few years, and it’s been working great.