Your premise does not work, you have to consider the things you can do in the location you choose, if the world were one homogenous blob who would care.
The second factor is what stage in life you are, young & unmarried might take you to places where it's easier to meet new people, young with kids you might want better neighborhoods and schools, middle aged an no kids, better access to cultural activities and easy travel, retired, better healthcare and friendly taxes.
Don't ski the trees, ski the spaces between the trees.
I basically said considering everything but skiing, where would you (you) like to live. It's a hypothetical. I never said the world was a homoblob. I'm assuming you will consider your life stage and everything else that matters to you except skiing.
"You just need to go at that shit wide open, hang on, and own it." —Camp
I'm going to have to think about this for a little while. Maybe Spain?
Can I be single and in my twenties again?
I'm with MikeK on the van dwelling life. If I were in my 20's and a set for life funder it's what I would be doing. It's what I hope to be doing part time once I'm done with school. I'll base out of Flag and hopefully get to the point where I have four day weekends that I can use to travel and explore the four corners region. If I were a twenty five year old funder I would live the gypsy life for years and not work, that's not my reality though.
Another dream of mine would be being that funder and traveling for many years with nothing more than what I could fit into my backpack. To walk the land every day but also be able to get a hotel room and shower at any point. That's my ultimate dream. In my twenties I was a real deal dirtbag ski bum and there is nothing like that kind of freedom when you have no obligations or restrictions. I didn't have a fund but I would work enough to eat and have some kind of housing but I wouldn't let myself become locked into anything that made it impossible for me to just pick and go whenever I felt like it. My fondest memories are of hitch hiking across states such as Utah, Colorado, and Wyoming with my back pack and ski gear. We would sleep under the stars without a care as to where we would be the following day. Most people don't even know what that kind of freedom is really like and now that life has got a good hold on me I doubt I'll get to experience it like that ever again. This is why I said in a another thread that I think our society puts to much pressure on kids to get focussed on a career and have them believing that retirement is so crucial. Having experienced that kind of freedom all of that other bullshit doesn't look as attractive as they want you to believe it is.
So back to the topic.....Spain, ya I'm going with Spain for now. There are topless beaches filled with beautiful woman within an hours drive of alpine ski resorts or so that's how I imagine it anyways.