Walter Montego: Easiest way is to play the game through a computer yourself afterwards and see if the player made any mistakes. Most players will make a few mistakes.

in reference to your longshot vs safe... the computer would decide just as easily as any other move... with math.

For example if you had a choice.. keep the game 50/50 or make a move that is 30% likely to win and 70% likely to give the opponent a 70/30 advantage... what would the computer do?

move 1: 50%
move 2: 30% + 70x30% = 51%

Move 2 wins.

The human may think this is a difficult decision (because the %ages are hard to calculate so it feels like a gut decision).. but not the computer.