(For future reference, comments, suggestions, links, etc., are always welcome.)
Matt Kirschenbaum runs "Zone of Influence," a blog about board-and-counter wargames. While that's a little removed from my own interest in political/military gaming, some of the same issues are relevant in terms of game design. Here are a couple of his posts dealing with two famous recreational wargamers, H.G. Wells and Robert Louis Stevenson. I haven't read either of H.G. Wells' books on the subject (Little Wars and Floor Games), but the article about Stevenson he links to is wonderful.