Trouble is a point game in which your actual score isn't relevant, at least not directly. Players shoot for a set amount per point, often a dollar. Thus, a player accumulating three trouble points owes each of his opponents three dollars. A player can erase all the points accumulated on a given hole by making par. At the end of the round, simply net all the points against each other and settle up.
Trouble is an excellent game for the intermediate player.
Often, such players are feeling pretty smug as their handicaps drop, and they need to be taken down a notch or two. Chicago Chicago is essentially a creative handicapping method. Wagering can involve a fixed sum to the winner or an amount based on point differentials. You can also add a bonus for anyone clearing his hurdle. The other players must agree to the bet.