I usually hit over my handicap (translation: I'd like to win more bets...) - shouldn't my handicap index be higher?

Did you know that the average player is expected to play to their course handicap or better only about 25% of the time? Remember that your handicap index is based on the best 10 of your last 20 score differentials. See the FAQ on how a USGA Handicap Index is computed for more information.