First of all, a PC24 to get around. If I won enough $$$, I'd even see about paying them to certify an extended range version for long over-water flights, to get to...
My vacation home in Hawaii. I might keep an Extra 330LS out there for tearing up the sky with when I'm there.
Then, a vacation home out in Couer d'Alene, or Sandpoint, or Alpine, with a Carbon Cub or a C185 for bopping around all the wonderful backwoods mountain strips up there.
Then, another one somewhere down in Texas so I could visit all the wonderful people there more frequently. And eat lots of brisket tacos.
I'd keep my current house to make it easy to visit friends and family here.
I'd have a fleet of Teslas to keep at all the airports I went to to get around.
And, I would travel the world in the PC24. First trip would be to load up my parents and my in-laws and fly to (and around) Europe to see all the world's great orchestras in their great venues, eat lots of tasty food, see the sights...
I'd probably spend a good amount of time exploring Australia and New Zealand, and some of the south Pacific islands as well.
Not that I've thought about this at all...