The whole trap and perception thing might be a subset of this : unskilled individuals assess badly their probabilities of success/failure. Usually they are way overconfident.
Simulating this is easy with GM lies and ruthless reality twisting. "You can totally take them alone and disarm them. Do you want to do that ? Describe your first move (then interrupts:) only your first adversary is quicker than you and cuts your hand. What do you do ?"
Any other option with more "fun factor" ? And possibly not a specific assessment move ? I am stuck.