hey @chrismorgan, this is really valuable feedback, and I intend to explore these suggestions for my own site, and future articles on the topic. I've just recently converted every post to have an assigned whostyle, and this seems like the right way to set up the CSS.
Another issue I'm focused on right now, is how to exchange these whostyles in a way that allows for automatic moderation. @kickscondor suggested JSON as a way to format CSS in a more parse-able manner, and I think that approach might be the easiest way to trust my server to only save received CSS rules that are (relatively) safe.