I haven't, but my brother has an A&A itch he's trying to get me in on. That particular one was a much longer project than I'd prefer to take up again (basically did it to teach myself Inkscape; ideally I could use Illustrator instead as it's worlds better. Even just regular AutoCAD would probably have been easier for me), but I'll probably turn something out someday.
ED: Found this, which does for A&A basically what the map I used (with the author's permission) did with risk but and hasn't been prettyified yet. I'd probably use that or make a full-version A&A as a base (IIRC, doesn't A&A have, like, whole separate games for each theater of the war?).
It depends on the game you play. I have regular World 1942 (several editions), Pacific 1940, Europe 1940, Battle of the Bulge, and Guadalcanal. It really depends on how into it you are, as each game has its own rules, and Guadalcanal and Battle of the Bulge are VERY different, but Pacific and Europe are just expanded versions of the regular game. They can even be combined into World 1940, which is HUGE, and I would imagine takes 20+ hours for a short game.