DoUEvenLoopBro,

You are saying you want to buy an airplane that carries passengers, luggage, and skis. This assumes you have the money. If you have the money, go for it!

It definitely sounds like you need cabin class. The Navajo immediately comes to mind. I am reminded of Lynn Johnston, the writer of the cartoon strip, For Better or For Worse.

For Better or For Worse by Lynn Johnston | Read Comic Strips at GoComics.com

One time she wrote that her real family had a Navajo, and they sounded like they were very happy with it. It gave them the freedom to pick up and go anywhere within range at a moment's notice. And they live in Canada, so they probably have a lot of winter ops experience. (And she writes a popular, profitable comic strip, so yes, they can afford it.)