How good do you have to be? Well, if you can figure out how to play the AI, you are half way there. Notice, I did not say you have to BEAT the AI. Just play it. The second half is to play online. Once you figure out that the game timer is per player, you are set!
If I need to say it again, I'm in.
Look, don't worry about winning Twilight Struggle Tournament, worry about learning Twilight Struggle through Tournament.
Also, does anyone know if Twilight Struggle games are record-able? Somekind of program that I could watch them later?