I think people are generally good at 2nd order thinking, and thinking within complex systems with multiple causes, effects and subsequent effects. Especially so if we're immersed and experienced in a field.

We are bad at thinking this way in groups, relatively. We're especially bad when these groups are political. If we're deciding on arming rebels, the political dynamics are the 2nd order effects that dominate thinking, not the war... especially if it's a small foreign war that's unlikely to reach home.

The rebel field commander has no problem recognising these strategic dynamics.