After reading the wall of text I find that I am even more interested than I was at the beginning. This has a lot of potential and if possible, I would love to make a swordsman class character. 

The idea of having an AI observe you, and then tweak your character into certain niches, would allow for no two characters to be exactly the same. Also the blissful unaware NPCs would make for a great twist for players. I like the emphasis on the choose of traveling in parties/soloing to complete dungeons/quests, and progress their gear and skills to better ranks. All the while that AI is noticing key points in your battles and further customize your class to fit your needs.

edit- I think the ooc is a good idea.