The biggest miss from Tailwind is ignoring the rest of the ecosystem. Rightly or wrongly, everyone has moved on to using shadcn's system for components. Tailwind hasn't. Tailwind has excellent components available through Plus which are worth paying for but they're not available where people are, which pushes people towards other libraries built on top of Tailwind. I have paid for Tailwind Plus and I like their Catalyst UI and I have used it on a project but it's a pain to use compared to alternatives, so, I don't bother.

I'd go as far as to guess that their revenue isn't down due to AI but because of their lifetime access model combined with shadcn's registry system being much easier to use.

Prediction: Tailwind acquired by Vercel.