Extreme Chess (Fritz) is very very good in analysis. It even analyze moves you don't play.
Chessmaster 3000 + is very good at "natural language advice", converting number crunching into a folksy probabilistic way of speaking.
Keep in mind, the greatest software series Chessmaster went out of business.
It's not like chess is the hottest thing.
Yeah but those are just using impersonal engines that analyse on game by game basis. It doesn't care who you are. That's not coaching. Just finding the best moves. A "real" AI chess coach will look at the games based on the individual. Remember styles and characteristics. Where they are weak at etc. And find remedies like puzzles based on the exact weaknesses.
Is anyone working on an AI Chess Coach which will analyse recent matches and distill the information into advice on how to improve? I'm guessing that this must be on Chess.com's radar.