To clarify, the bit where I think the bitter lesson applies is trying to standardize the directory names, the permitted headings and paragraph lengths, etc. It's pointless bikeshedding.

Making your docs nice and modular, and having a high-level overview that tells you where to find more detailed info on specific topics, is definitely a good idea. We already know that when we're writing docs for human readers. The LLMs are already trained on a big corpus written by and for humans. There's no compelling reason why we need to do anything radically different to help them out. To the contrary, it's better not to do anything radically different, so that new LLM-assisted code and docs can be accessible to humans too.

Well-written docs already play nicely with LLM context.