If I won the powerball I'd hope to find faster transport than a Shorts Sherpa. I too would think about Bmers, but also about the Hayes Diesel KLR (only $18K) because as rich as I may get, I'll always be the guy who ate one bean burrito and a small coke for lunch in college because it was less than a buck and I was cash strapped. Sure I could buy other bikes cheaper, but which one would use less fuel per mile or give me a longer riding range?
As far as the destination goes? The northern most point of Alaska reachable by plane/motorcycle. I'd start when the snow fall quits (or is at least very intermittent) and ride south until I couldn't get further (like to get picked up there and flown to antartica for a brief ride). Then I'd like to ride one of the trails through the rockies and the appalachas on a Super Sherpa or TW 200 (sorry, I love trials bikes but their lack of range and seating is a deal killer).
"My KLR belongs to God, when he wants it clean he washes it."