Khan suffers from much the same problem that would render Sherlock Holmes incapable of solving the simplest crime if deported to today: he's a fish out of water. He may be tactically brilliant in 1990s style warfare, but (in the original timeline) he has mere hours to adapt to the 23rd century in "Space Seed" before being defeated by veterans of that style of combat, then spends fifteen years stuck on a planet with no institutes of higher learning for aspiring strategists, and then again only has hours to come up with modern ideas.
Then again, Khan does appear to be a sponge for information, while Holmes was described as unwilling to learn anything new (at least outside his own profession, and he already knew everything about that!). Given a few more hours, he might have come up with something more workable.
In ST:ID, Khan does appear to have come up with a rather brilliant plan. Despite being vastly outgunned by his enemies (essentially the whole universe), he manages to escape from Admiral Marcus, get hold of his 72 helpless compatriots, and almost escape with them. It is an extremely complicated plan, yet it works seamlessly, against enemies at least as driven, quick-witted and/or forward-planning as himself. But his brilliance is countered by his other well-established quality, the arrogance that makes him underestimate Spock at the crucial moment.
It would be inconsistent were any of our heroes to come up with such a complicated yet successful plan - they are more the reactive type. But Data might just barely qualify: he would be the one to see the challenge as a chess game of complex moves and countermoves, something he is especially qualified to tackle, while somebody like Kirk or Picard would think that no plan survives contact with the enemy, and even Spock would acknowledge the logic of dealing with the present first.
Timo Saloniemi