As a BSD user, I can't help you.  As a chess player, I will comment that
there's a certain learning curve involved, and playing against random
moves isn't going to advance you far along it.  I've never known anyone to
become even moderately facile at chess without getting their head pounded
in on a regular basis.  If you or your son's ego isn't up to that, OSB
(Other Sports Beckon).  ;)

Point well taken. ;-) But...
It's not that either of us mind losing per se. What I've discovered that gnuchess and crafty are orders of magnitude stronger than the old program we used to play against.

Say you want to learn to play tennis. You're just beginning. Who should you begin challenging in order to improve your game and enjoy yourself while doing it? Andy Roddick or the friend who's been taking intermediate tennis lessons through the city rec dept? In this analogy, the standard chess engines are Andy Roddicks and our old program was the intermediate friend.

My son is just not gonna learn that much nor enjoy himself much playing against Andy Roddick. I don't want his first serious foray into computer chess to be *that* intimidating or demoralizing.

That said, the MOST frustrating part of learning chess is usually
tactical, not strategic (inadvertently throwing away pieces).

That's it exactly.

There are a
number of good web/Java based free chess games on the net - have you tried
any of them?  Many will show possible moves, blink to indicate pieces at
risk, etc.

That sounds great! Do you have any suggestions off hand? I thought my searches were pretty exhaustive, but I didn't come up with anything like what you're talking about.

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