Very well observed. I found one more thing: they fail to consider what a 3rd person might understand from your conversation, so when you ask it to dump stuff into a Documentation, they keep making references to facts you had previously discussed or to the train of thought, completely irrelevant to bystander.
100% -- this is the worst. Referencing all sorts of "words with made up contextual/analogous meanings" based on the conversation...outside of the conversation.
Does anyone have a read on if this is primarily a Claude issue, or if all LLMs do this?