This probably wouldn't be an extremely complicated addition to the game. How about a simple +/- dollar amount of your total winnings or losses at gambling, including the Hartys?  For example, if I have played x number of games of blackjack and came out $10,000 ahead, and contributed 5 million to Hartys and won 6 million, my gambling prowess would be +1,010,000 (All winnings minus all losses or Harty contributions).

It could appear on the profile or in the Bookkeeper's data. We could discuss how or where the data is shown and utilized.

Thought?

+1 for this, it would enable people to keep track of their crippling gambling addictions :P