When it comes to chess it has been my experience the more your Sim 'practices' with other Sims or plays against others Sims the better they become with the game. Playing chess on the computer, I think, is more geared towards building the logic skill. I have a teen with this lifetime wish. I send her to the park on the weekends to play against other Sims because (for me) it raises three skills at one time (Logic, Charisma and Chess). When she challenges another Sim, I always host the game at my Sims home, less distractions. :)