I think nowadays you can break it down pretty easily.
If you like cosmopolitan living with non-stop vibrancy and being around lots of people, any of the major cities of the world near coastlines should do. You can't really tell one from another, except of course for the weather variances. So then you just need to decide what kind of weather you prefer. Most coastal cities are fairly close in terms of weather patterns. Australia's beautiful Gold Coast is a lot like Florida's style for example. New York is one of the greatest cities in the world, but it comes with quite a bunch of neighbors. LA, San Francisco, San Diego are all beautiful places to live. I have friends in London who think there's nothing quite like that city and love the dreariness and constant rain. But cities are cities for the most part.
If you like more relaxed living, but want to still be close to the action, most of the major metropolitan suburbs of the big cities will work. Again, they all look alike for the most part, shopping malls, chain restaurants, movie theatres, parks, tourist attractions, freeways, etc. and you just need to decide on the weather factor. Suburbs of Philadelphia are beautiful. Suburbs of Los Angeles are great. Long Island, White Plains, Scarsdale, all nice suburbs of New York, along with parts of Northern New Jersey.
If you like peace and quiet and could care less about being close to things, head for the deeper inland parts of any of the great countries of the world. Get a nice ranch, where you can't see your neighbors, wake up to the birds and total tranquility, clean air, no need to drive anywhere, etc. In the US, places like Colorado, throughout the midwest, upstate areas of the east coast, are all easy living with minimal stress. Canada has some incredibly beautiful interior areas.
I really love the US. Its more diverse than anywhere else I've ever seen. So the good thing here, you can find exactly what you want because the variety is extensive and covers all three of the broad sprectrums above.
So really what you should decide first is the exact climate you prefer and then go from there.
Personally I'm a big Florida fan now. Its got everything you can imagine except snow and cold weather, which are always just a plane ride away if you get the urge.
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