Plane? The single pilot would need to be somebody other than me! Ha. Done with that experiment. In my experience being a pilot is great, if you start as young as you can, fly all the time, and develop incredible instincts. I had friends tell me how much I would love it, many because I have a lot of experience on the water in some very dicey situations. But nope. spooked twice and grounded!
Now If I could have pretty much any decent jet that didn't need too long a runway, and could keep the two pilots employed to tune skis, etc., sign me up. So easy to get spoiled flying that way.
We have out favorite ski car, our third Toyota Land Cruiser. Have no interest in anything else, at all. Have tried others, and this just works for us. Part of my bias is it's simplicity. It "wears well". And knock on wood in 600K+ miles of driving, they have been ultra reliable. Since we don't have too many Porsche, Audi or BMW techs near our ski locations, I need to consider that. We have never wanted a Lexus version as we frankly did not want the badge. I've driven one from Boston to Alyeska. 1200 miles a day. That is my ski car. Incredibly comfortable, and with four studded Hakka's, it is a tank.
A BMW MX5 would be tempting. No thanks on the Range Rover. I think there is one in every third driveway at home driven by a 30something stay at home mom in yoga pants.....that's not me! Pretty cush interiors, though. Surprised they let all of those golden and labs ride in them. No matter how great they may be, can't do it.
Now a summer car? MUCH longer list..........Just give me $250K and let me spend six months on Bring a Trailer. I'll figure it out.