The narcissistic in me (OK, me) is always tempted by those "best city" or "where you should live" lists. I know the problems with my region and its many loony-left governments, and that the weather gets old this time of year, but still like to see "my" hometown or its suburbs rank high. (And for good reason, I'd still argue.)
But the answers are baked into the hardwear. The guiding criteria behind each list determines which towns will appear in what places. And they seldom care about what matters to me. How could I live in a city that was all flat? Or far from the sea? Or had only one season? Or too many shopping malls? Or was soul-crushingly boring? But other people care more about health services, convenience, safety, or maybe parks, theater, music . . . People also have different food tastes. And isn't the best city where your loved ones are?
No one can make a list for everyone. Nature (or Nature's God) provides a more rational voting mechanism: our feet.
You may get priced out of San Francisco, but you can pitch a tent on a sidewalk. To paraphrase Pascal, everyone seeks happiness, even when they move to Portland. Even our most "masochistic" and "forced" choices ultimately derive from our desires.
Plato refused to leave his home town, even when its leaders decided to kill him. Chesterton said that when you love a country, or a city, whatever it was before, your love makes it beautiful.
So no objective list of "best cities" is possible, only subjective, and patriotic, bickering.