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Yes, the new Chessmaster, which is available for PC and for PS2/Xbox - the PC version is $30 and the console versions are $20 - is a very, very good chess teacher.
It has a fairly in-depth tutorial, even going into teaching standard openings, and has a fairly good set of AI opponents with whom you can play. It tracks your progress and suggests which opponent you should play next. Each persona even has their own personal quirks, which is really neat.
You can even check out historical games of chess, with commentary and notes on the moves and the strategies. There's a lot to learn there.
But for me, the neat thing about it is the fact that it works over Xbox Live. I haven't been on in a while, but there's a neat little community springing up over there.
I would still play with him in person, but when you can't get the time together, it would be worth it for both of you to get in some Chessmaster time. It's pretty cool.
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