A squillion dollars You say....Why buy anything,You're never going to be satisified with what You have , You get a G5 then the g6 g7 and so on and so on.
You can go any where You want go first class
True, but then you're not tied to some airlines schedule, or surly staff. As far as the burden of ownership, that's what staff are for. Besides, with your own a/c you don't have to deal with the riff raff that travel on airlines.
With that much money, I'd think I'd get me one of them giant Antonovs, put the G5, AB139, and turbo Beaver on floats inside.

Then I'm ready for any eventuality.
If it's only toys we're allowed to have then I think a stripped down AH-1 to take me somewhere hot. Enough space for a good friend, cases/keg of beer, case or two of great Scotch, and a snack for the trip. With a squillion dollars, I can afford to not need to take luggage. Just stock the lodge with clothes, or the staff can take care of it. Did I mention that I'd have a place in the Gold Coast hinterland, with a view of the Pacific, a hangar for the 139 and Ah-1, a 4 bedroom guest lodge, salt water pool, the biggest darn fish tank you've ever seen, a selection of the finest beverages that the land of the Scots produces, variety of the best barley pops, oh and hot tub ?? Oh and a paddock with a couple of horses, and so's I don't forget 407D, CTD, and Ned, in case they stop by, a couple of sheep too.
😉 😛 😀
Cheers