At the same time doing the simplest imaginable layout was a headache. I've done it, and it was interesting as in, this is a challenge and I am taking it head on, but it never should've been a challenge. Things have improved exponentially here, but it should've been the idea all along. Not how to cascade rules.
All other criticism, the syntax etc. is nitpicky and not important. As long as it's allowing you to do something useful without much fuss, I am ok with any syntax. But it didn't and it never did. Making a webpage layout should not be a full time job.
There used to be DSSSL and JSS. The former came out if the SGML world, like HTML itself, and it was kind if the obvious solution to adapt it for the web. The latter used JavaScript syntax and was Netscape's favourite, which also made sense, them being JavaScript's inventors.
(A maybe interesting aside to this story is that JavaScript actually predates CSS, at least if we go by the dates each shipped in a browser.)