Milo switches to be Neutral Good over the course of the first two books. I forget if I mention that specifically or if it’s simply implied, and mentioned at the top of the character sheets.
As for him and chess, I can’t remember if that’s a plot hole or supposed to be Milo trolling people in the Duelling Club. I’ll look into it at some point, but any time I spend fixing stuff in the past is time I don’t spend working on the new chapter. It’s a very frustrating dilemma.