Wow... quite a thread.
So I'll add my thoughts around a few of the topics here. Is it in theory possible to create some form of simulation/machine learning/learning AI based on trying to generate lots of played games and having it improve based on patterns of those games? Yes.
Now is it feasible to do that with any reasonable amount of resources/time that would actually produce a useful result for a complex TripleA map? Personally, I don't believe that it is at this point.
Breaking that down a bit further, if you say took just 1 TripleA map say revised, removed 95% of the starting units, reduced overall territory production values to 20%, changed all sea territories to land, removed all sea units, and removed all air units then created a base AI that understands the rules then optimized the performance of that AI then acquired significant compute power and data storage then you could probably create a some type of machine learning AI and if anyone really was serious about doing it that is essentially where I would recommend starting with a very stripped down version of a single map to at least prove they can do it with that and see how long it would take.
Even if you achieve an expert level AI on that stripped down map, being able to then do it for Global or Total World War or Civil War would be orders of magnitude more difficult and require a lot more time and resources.
So IMO, that mostly leaves us with trying to make some form of weighted and limited simulation AI which is what we have as a base today. If done right, this could be improved to beat 99% of players and run within a reasonable amount of time. There is already a list of items that could be improved/added and mostly we'd need more people to post examples of where the AI makes poor decisions.
I would love to focus more on improving the AI and that was what originally brought me to developing TripleA as the previous AI was... well... terrible. Ideally I'd really like to just develop the AI and create some maps but given that we only have a few developers working on TripleA in their spare time, I end up working on a lot of other things around the engine and bugs.