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I've done something similar to this in my fictional save.
I use a program called "OpenCode" and just have it point to the import/export directory of my fictional save. So, then I export the roster file for the entire organization with a view that has all the stats, and just tell the AI to analyze my organization from the perspective of an assistant GM.
Another thing I did was took a screenshot of my baseball park's park effects and dropped it into the import/export folder as well, so the assistant GM will also take into account park effects.
It seems to do a reasonably good job of helping me with analysis, like an assistant GM should.
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