I’m not sure if it would fit into your dev stack, but letting Tailwind be handled by a Makefile might help. Or, really, any build tool that can use timestamps to determine if a build is needed.

I’ve got a setup like this for a couple Eleventy projects, where it kicks off ‘make’ before starting the dev server. Most of the time, make will finish instantly because I haven’t changed the CSS source. Here’s the file I use in case it helps: https://gist.github.com/dceddia/be4d0f136a340359a57a52f16893...