All ways he can spend the money with the guidelines
For fun, I made a list of things you can spend the money on, and they are all valid by the movie's rules. Since it was in New York, I made some of them New York related.
1. Rent out lots of hotel rooms and let people stay in them
2. Pay for tickets to ball games
3. Rent a huge billboard
4. Pay to talk and advertise on the radio
5. Buy people food in insanely expensive restaurants
6. Pay for sex for yourself and others at the legal brothels in Nevada
7. Go to a gun range and shoot with a rented gun and buy your own ammo and targets
8. Pay for gas for NYC taxis and busses
9. Buy fireworks and blow them up
10. Pay for massages for people
11. Buy tickets for everyone to movies
12. Buy admission to theme parks
13. Buy plane tickets for people
14. Go to the busiest bars and say "Its on me!"
15. Go to a strip club and spend hours in the champagne room
16. Pay people's parking tickets
17. Pay people's hospital bills
18. Pay people's student loans
19. Pay for concert tickets for people
20. Go to an arcade and keep losing to pump in more quarters
21. Buy lots of expensive stamps and mail them (in the movie)
22. Buy gold and diamonds, go to a pawn shop, and sell them for a hit from the dealer
23. Throw huge parties in fancy hotels, catered by fancy restaurants with the best booze
24. Get a lawyer to advise you and pay them a ton for it
25. Pay people's bail who have been arrested
26. Hire several bodyguards
27. Buy tons of expensive candles, light them, and let them melt
28. Buy everyone tickets to Broadway shows
29. Pay admission to all New York attractions i.e.. Empire State Building, Statue of Liberty, and museums
30. Rent lots of movies and return them immediately
31. Buy food for the animals at the Bronx Zoo
32. Pay people to slap them ( $10,000 a slap)
33. Hire a famous band to play a private concert
34. Gamble away the allowed percentage
35. Donate the allowed percentage