My question is: Can anyone point me to a Kriegspiel-style PBEM wargame that is fully automated? That is, a game in which the orders are interpreted by a computer?
The Combat Mission games (www.battlefront.com) sound like exactly what you're looking for. From the web site: "Combat Mission is a 1-2 player, turn-based, simultaneous-execution 3D simulation of WWII tactical warfare."
What that means is that you and your opponent do your orders, send them to one another, and then the computer executes them simultaneously and shows you the results.