Steamboat Springs, Colorado (But I would settle for Denver). World class skiing. An awesome town. It is absolutely beautiful. I go on vacation to Colorado every winter for a long ski trip, and have never felt the desire to get out of there. Colorado has it all. Awesome winters, awesome summers, awesome beers, awesome people and pretty sweet fires. And some day I will live in Colorado. If things continue on the path they are on now, I should be ready to start a family in ~5 years. And God willing the family would call somewhere in Colorado home.
If anything I would just move farther north to a less populated area here in Minnesota (can you say... lakeside cabin?). I love this state, enough said. If I had to get my ass outta the states, well, I've only been to one place abroad but I would have no complaints if I had to return. That would be Brazil's coast near São Paulo. Spoiler Can't complain about this. Crime issues and gang presence may be a little heavy but otherwise it was gorgeous place, the people were friendly (and beautiful), and the economy in that area is BOOMING so there'd be jobs and money to make. I already speak Portuguese too so even though I'm a super-gringo, I could get around. Yeah Brazil is friggin' awesome.
Like many people here, I don't feel the need to leave the US. I'm extremely happy in Chicago and think its one of the greatest cities in the country, however, I think any move would depend on a timeframe. I loved my time living in NYC, but could only do it for a few years. I'd probably choose either Denver or Charlotte. Love everything about Denver and its still developing. My family almost moved to Charlotte when I was younger and I still don't think my Mom has forgiven my Dad for turning the job down. The climate, people, and cost of living, can't beat it. For a more aspirational thought, London for sure. The weather would take some getting used to and the cost of living is ridiculous, but I'm borderline obsessed culturally and my two trips there have stuck with me more than anywhere else I've been. I'd consider the southern coast of Spain as well. Food, culture, women, weather, women, it really has it all. And I've never been, but everything I've heard about Stockholm has been brilliant and my parents raved about their trip to Norway/Sweden last Thanksgiving, so that could be an interesting thought as well.
I can't get that app to work on my Macbook, but I wonder whether it's calculating based on SF proper...which includes a lot of fairly poor areas that probably, artificially, pull the COL down....maybe Brisbane proper has the same deal though. Anyway, I know tons of folks in the Bay Area that are sacrificing pretty heavily (housing, entertainment, school district) to live in the area...heck, I guess that's the situation we were in when we lived there. And all the while, you're surrounded by lots of young folks living quite well and have no problem doing things like making all cash offers on $.5M condos and driving their Teslas on Friday and eating at the French Laundry. So I'd count SF as a city or area that you'd want a lot of money to live in.
I don't want to leave the U.S. but I sometimes wonder why I had to be born in the suburbs of Philadelphia when there are probably a bunch of better cities to live in. I've vacationed in Ft. Lauderdale several times and never want to come home when I'm down there. I love the beaches and the atmosphere is relaxing unlike Philadelphia's "everything needs to get done now" attitude. If I could look at the beach all day everyday and never see snow again I'd be so happy. I don't care if that's cliche.
Putting aside all the dingos eating your babies, and shit. As others have mentioned, the Mediterranean coast of France would be fantastic. The landscape, the weather, and I could endlessly indulge my love of good wine and good food. And I hear I can go on strike any time i don't feel like working. Unfortunately, the place is lousy with French people. And I think we all can agree that the Germans are coming back someday.
I had thoughts about London, New York, Melbourne - that kind of thing. But honestly, I could move (back) to Singapore and be happy. Amazing city. It's easy to travel from, there's a strong economy, the government is concerned with long-term development (and judging by the development in the last 20 years, know what they are doing), there are good schools there for any minime that pops out, great food and a varied night-life. Oh, and no winter.
Jersey. Not New Jersey. Bailiwick of Jersey. Old Jersey. Island in the English Channel Jersey. It gets all its money from tourism and financial services, so taxes are incredibly low, the standard of living is high, and you can easily travel to England and France, or wherever else in Europe.
Sweden. If I am stuck in a place forever, I want it to have hot people who are cold enough to want to warm me up all the time. Also a diet heavy in fish so I get all my good vitamins, and wonderful education and oh yeah, did I mention the hot men? I don't even know how to make decisions without hormones.
I would live inside Roxanne's ass. Sure it's tight (hind)quarters and a bunch of dicks are always knocking at the door, but it's cozy and the architecture is stunning. Plus it's located in a good school district.
Even though I'm susceptible to getting sick from the heat, I would like to go live in California or even Arizona one day, if even for just three months. That being said, I'm all for a colder than a witch's tit all year round country, like Norway, Iceland, Finland. Also: Australia . For the women. Would need to toughen up, though, for all the insane wild life. New Zealand is beautiful as well from what I've seen in pics and in Lord of the Rings.