Assuming you already have retirement money all setup, and this is truly expendable money, then you got to go with what brings the biggest smile on your face. I would certainly recommend a few machines, since you are here, and obviously pinball brings a smile to you. But I would also recommend taking some of the money and having a great time with your friends and family (not necessarily at the same time), and create some truly great memories to carry with you over the next decade. Those will mean something to you when you cannot focus on the pinball machine anymore