Each group does it differently. This group I'm asking about that is planning on going to Pinehurst, the getaway is really more of a beer drinking and poker playing weekend with the guys with some golf, to be honest. Inside of the cost of the trip in which the Commish handles all the money for everything, he will charge each participant around $50 for the group bets. On the Saturday rounds, we will play a gross score round on your own ball and pay off the Low Gross and a Blind Bogey Low Net Winner in the morning. Then the highlight is the afternoon Scramble round in which on Friday night there is a draft of the teams which is a blast since everyone is super drunk and a ton of trash talking is going on (I told you it was corny). The foursome winning the Scramble is the big thing and there is payoff. Also during the Scramble round, we have a Closest to the Pin and a Long Drive contest. And the last payoff is a Trophy for "F$#k you are Awful" award and the stories are hilarious as there is a ton of embelishment going on in most years. In addition to the Saturday round official playing of the trip, a lot of guys play on Thursday afternoon, two rounds on Friday and in rare occassions, a Sunday morning round. And there are various side bets and match bets of all kinds going on but these rounds are not organized with the betting. And again, the golf is there for the beer drinking (and cigar smoking for those that partake) mostly.
I don't do any of the organizing; I just show up and have a blast and then write the Commish a check for whatever it costs a month or so later when he communicates.