One trip I was with someone who went down with $2000 cash. He lost almost all of it within a few hours and decided he wasn't spending any more money on the trip. He stayed in the room for three days (to be fair, it was a Cosmo pent house). I'm like "dude, wtf???" I understand being dead after a few days of partying and not wanting to do stuff then. Even I was tapped this trip after two nights. But to fly in, lose half your bank roll in an hour, and then decide you're not doing anything is a **** move. It's why I stopped going with gamblers. It's a gamble in itself. If they win, awesome. If they lose, then they might as well change their flight and go home.
if your dude is dropping 2k in a few hours, either he aint broke and he can afford it (and not asterisk out of the entire weekend), or he has a gambling/self control problem and needs to check himself
I don't make $$$$$ and I gamble, but I keep a budget for how much im willing to blow each night. protip: keep your nightly bankroll in separate sealed envelopes, give em to a friend if you have to.
As for crew size, 6-8 is about right. Most of the problems are logistics like transportation/rooms, scheduling (making sure we have the same days off), etc. Caviat though...no randoms. Crew/close friends only. No friends of a friend of a friend, random coworkers no one else has met, girls' cousin visiting from out of the country, etc. We can chill but they need to handle their own business.