Money is no object, huh?
Okay, let's see...
1. Summer residence would be an estate/winery on a vineyard in the Sonoma or Napa area. I'd hire a top winemaker and crew to run the winery part of it, since I know nothing about making great wines, I just enjoy drinking them
2. Winter residence would be a large custom mountain lodge (possibly log home) on acreage near Vail. I'd spent the winters there and enjoy the ski season at the various ski resorts along the I-70 corridor in Eagle and Summit counties.
I'd also have a few nice pieds-à-terre throughout the world, so I have my own places to stay when visiting. These would be large condos in the heart of the cities:
New York City
And with that kind of money, I'd never fly commercial again, so I'd have my own private jet and crew. Maybe two...one large enough to travel the world in comfort, and one small enough to get in and out of the Eagle County airport in the winters.
Now to solve the "money is no object" part...