I would buy up all the water within a 100 mile radius of Chaotic's house. Take care of my father and stepmother. Then vanish.
Buy a large piece of land for wildlife management and build a modest house in the middle of it, and I mean I'd build it. Probably have to do two as my wife likes the ocean and I like the mountains. Get a motorhome and travel around the country and take a couple dive trips each year.
There is a whole great big world out there, and I would see a lot of it. After that wanderlust abates, a nice, average house up in the Adirondacks for the summer, and somewhere warmer for the winter. Of course, toys, but not as many as you would think....
Pay to have every bike at the GNF's torn down to it's individual nuts and bolts. Then pay Ulrich enough to produce an end of the year disgraced racers edition of Road Racing World. Seems like a really entertaining way to waste a bunch of money.
Pay off my debts. Pretend it didn't happen, but say "I wish" and "no" a lot less often. I'm not even sure I'd move. I'd do all the "I wish" projects at this house though. I would make sure some friends and family members who have been there for me don't have mortgages or car payments. Maybe create some trusts for a few of my friends' kids. Anonymously if possible. People don't ask for money if they don't know you have it. In a weird way, I'd basically be laundering money through my law practice to keep my friends in the dark on winning. Be philanthropic. Buy every motorcycle under $2,000 on Craigslist. Start my own spec 250 series after repaving Nelson Ledges...
Oh, I'd buy all my groomsmen the cars they drove in high school. I feel like that would just be too funny to pass up.
Quit my job...while I love it sometimes..I don't love it THAT much. Then A trip to the Bunny Ranch A trip to Amsterdam A Graves Yamaha R1 with lots of spares, or one of Mr. Ulrich's GSXR1000's set up for me. Or fuckit..BOTH! A bus RV like Broome's and a big fuckin' trailer behind it to haul my toys. Raven's club level season tickets. A ZL1 Camaro A private guitar teacher so I could finally learn to play. And last but not least...I'd buy my ex wife's house and evict her fat ass!
You need to include a trip to a doctors office for meds to clear up the shit you picked up on the first 2 stops of your adventure.
Man, my buddy and I have this conversation almost every time the PB or MB is up into the 100's of millions.... Lotsa fun to dream about this and at the same time very depressing.... DIT's if you don't know the song, give 'Buy me a boat' a listen....