Systems in accordance with embodiments of the invention include: a gambling game; an entertainment game; and a game world engine constructed to communicate, to the real world engine, gameplay gambling event occurrences based upon a player's skillful execution of the entertainment game that triggers a wager in the gambling game, the game world engine utilizing a skill calibration module constructed to receive, from the entertainment software engine, player performance information for the player, analyze the player performance information to determine the player's skill level in playing the entertainment game, determine whether the terms of the wager of the gambling game are calibrated in a manner appropriate to the player's skill level in the entertainment game, and send, to the real world engine, a command that causes the real world engine to calibrate the terms of the wager in the gambling game.