Hi, you have a lot of ideas there, some are not really practical. Some of the more natural techniques are not available in assistant methods.
I believe you are on the best path of those that are offered - instructions (which is equivalent to, but not exactly the same thing as, “system message”.)
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You need the AI to always know certain information;
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You cannot rely on document retrieval, as it is based on user input and the report may be displaced by other files when loading the AI context;
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You cannot place messages in any other role than “user”, and user messages may expire from chat history at unknown point in time;
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adding continued information injection via user messages will place them in threads, blowing up the size quickly.
Therefore, the one persistent place without duplication is in instructions.
You can decide if per-assistant is what you want, or if it should be the instruction that overrides assistant programming per-run.
Perhaps OpenAI would see the light of a “documentation” message role. One specifically for automated knowledge injection, recognized via training as being useful for answering the latest question. One an assistant doesn’t need beyond a run. This works well in my own -instruct chatbot employing emulation of ChatML.