If I win the lottery, there will no new jet or yacht ownership. Boiler would instead become a renter of nice things, but would never go as far as renting a yacht/jet.
I would move to first class when flying. A nice new car would be in order, but something in the $60,000 range.......................certainly nothing as expensive as DD's Duesenberg Model J Phaeton.
I would rent some nice homes and condominiums much more regularly than I do now. Isla Mujeres, MX, and Pensacola Beach would become two mainstays for me. I can already feel the sun.
Much more golf would be in order, including a new country club membership. I suspect that I would continue to banter on LVA.