Getting around the Limited Gambling clause and Limited Gifts clause?
He's only allowed to waste 5% ($1.5 Million) on gambling and limited on giving gifts, right.
What about making stupid bets against his friends that he'll lose on purpose? Technically within the rules and he keeps some good will with them so they don't think he's as crazy.
"Hey guys. You fifteen people are my closest friends, but don't think that I'm just going to let you mooch off of me. Now that being said, I'll bet you each $100,000 that I can run around Central Park in less than 5 minutes."