Chess as a game sucks because it doesn't have any handicap.
Pool, for example, is nice, you just tell your handicap, and you can have a nice and challenging game between two people of different skills.
Same for Go the board game, you just tell your rank, and the opponents rank determines the handicap.
Same should go for TW multiplayer, you play a game and see how much more money you need. For a game with 5000f for both, a 1000 bonus can make quite a big difference in the field. If the opponent is better, then the money does balance it nicely.
Just remember, the handicap is there to make you even, or near even, not to make you overpower him.
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