Easily spend 30 million in 5 days or less
Following all the guidelines:
Day 1:
Go to the casino, bet 1.5 million on a single game. Chances are very good you will lose.
Then go to a local charity and donate 1.5 million.
This leaves only 27 million to worry about.
For day 1 through day 4, you will hire The Eagles for private shows at small venues of your choice. You won't have to pay for the venues because after the performances, it will hit the media and those clubs / bars will see business increase. BTW, The Eagles charge 6 million dollars for a private booking.
After 4 days of shows, you just spent 24 million on them. Are you getting your money's worth? Yes, because that's their going rate and you sit through the hour each night they perform. Even if you don't like The Eagles, it's a great way to dump the money and all within the guidelines. Plus, even though those guys are jackasses, there is no way in hell they can refuse 24 million for 4 hours of work. You could even call the shots on what songs make the set-list.
Last day, you have 3 million left. As it turns out, you can hire Metallica for 1.5 million for a personal show. Again, go to a club, book them to do two shows that day. The first show is entirely comprised of their cover songs from the old days. The second show is original material from the first 4 albums, another set-list of your choosing.
Boom, 30 million spent, got your money's worth, followed the guidelines. Hello, 300 million.
I will never have a sig line