Not really - the site is great as-is and there's nothing wrong with this approach. It looks like it works really well for Mr. 61.
But I'd imagine it'd be pretty helpful to write tools to help with maintaining the site which do leverage LLM models. Do a combination of search + AI to rewrite + reviewing the individual edits (e.g. through selective git adds). That's actually a plus in favor of flat files - it's all just code and the tools are plentiful. It's very "Unix" and hacker friendly.
I'm imagining a tool like https://github.com/paul-gauthier/aider (which I haven't tried yet, but it looks useful for this kind of effort).