With tools such as PostCSS, and servers serving zipped styles across CDN, maintaining a single request to the styles; does it really benefit from breaking up the styles these days?
Also, I’m going to assume, besides the core styles that run a website, anything that is loaded later can come in with its specific styles as part of the HTML/JS.
For the critical CSS thing, we used to kinda do it by hand with some automation more as a toolset to help us decide how much to include (inside the HTML itself - `<styles>`) and then insert the stylesheet. But then, we always found it better to set a Stylesheet Budget and work with it.