Mark Silcox and I are thinking about proposing either a "D & D and Philosophy" anthology to either Blackwell or Open Court. Basically while doing the two RPG chapters in our book we were forced to think a lot about D & D. In the Artificial Intelligence chapter we ended up posing the problem of AI in terms of what a human Game Master can do versus what a computer can do in the same role. In the chapter on the self we had to think deeply again about the differences in ways that humans Game Masters allow your character to do things that you can't do and the way computers allow you to do this (This theme is roughly one third of our forthcoming paper on Nozick's experience machine and World of Warcraft in the WoW and Philosophy anthology that Luke and John are editing.)
For a D & D book we'd like: (1) a person with no experience in philosophy or D & D to be able to read it and get a historically informed equivalent of an intro to philosophy class, (2) the issues covered to be ones that naturally arise from reflection on D & D, (3) to be such that players and game masters actually find improvement with their game-play from reading the book, (4) some of the papers to contain non-trivial philosophical theses. Here are some possible chapter ideas I've got.
Plato- Two critiques from The Republic: (1) role playing in the arts as epistemically bad compared to the kind of learning that leads to apprehension of the forms, and (2) role playing as morally corrupting.
Aristotle- (1) Four causes and kind of metaphysics presupposed in medieval university system (that fantasy novel universities tend to be based on). Possibly Weberian claims about "disenchantment of the world" when everything becomes efficient causality. (2) Virtue ethics and game-play basic stats as a theory of human nature (Silcox has cool ideas about this).
Medievals/very early moderns- (1) Polytheism in light of medieval arguments that God is one necessary being. (2) What medieval universities were actually like and how learning worked in them, (3) how early alchemy actually works and informs magic in fantasy novels.
Hobbes and Rousseau on the "state of nature" and how to model these things in fantasy world-building.
Hume and Logical Positivists- (1) Critique of miracles and how magic is supposed to work in fantasy RPG universes. (2) Critique of notion of "God" and RPG divinities.
Leibniz/Kripke/Lewis- Possible worlds as a way to make sense of what an RPG is. Also appeal to possible worlds within D & D universe.
Kant- Another critique of role playing as bad because consistency is necessary to moral development.
Mill and Kant- History of alignment in various versions of D & D (I think that law/chaos predicates a characters motives towards Kantian right and good/evil predicates a characters motives towards Millean good/bad.)
Kant/Cassirer- Transcendental Idealism sans necessary constitutive powers of the mind justifying new agey approaches to magic (this ends up being a critique of Transcendental Idealism sans necessary constitutive powers of the mind).
Marx and Marxists on class struggle and how to model this in fantasy world-building.
Turing- Game Masters versus Computers on the Turing Test (there's lots on this Mark and I didn't go into in the book).
I'll add some more to this list later in the day. Any other ideas? There has to be room for aesthetics proper.