I’ve actually live in Los Angeles most of my life and moved to Chicago (voluntarily) so my answer is Chicago. Although as I look out of the window on a May afternoon and see it’s grey and wet out, maybe I should have voted LA.
Roscoe’s is still ready for you whenever you come crawlin’ back, lady.
Seattle. Full of hipsters, but geeky ones. And less snobby than the ones in Silicon Valley. *
- Above perception based on surfing the internet and no actual real experience in either location.
Why do you list 16 cities but leave out the 10th leargest city in the USA- San Jose?
Kushiel- hipsters are mostly in SF, not SJ.
I live in Somerville now, so Boston was an easy pick. Would make my commute shorter. Plus it’s the greatest city in the world, especially in the spring. I love Boston in spring.
I have nightmares of hipsters in skinny jeans bitching about the humidity affecting their hair flip while snobbing over which cut of fish is best for their sashimi at Pike Place Market.
Humour, people, humour.
BOSTON!
Best little city ever.
I live in Denver now, and NY is definitely a favorite. But since I’m a parent, I’d vote Boston.
San Francisco. Perfect climate, cosmopolitan, good universities, not too far from LA to visit friends there.
I work there sometimes. Very dirty. Cold in summer. High crime. The government is both corrupt and incompetant. Rents and housing are skyhigh.
True, you don’t need a car*, which is good as it’s one of the most un-car-friendly places to drive anywhere.
*When Muni is running.
I clicked Miami, but I really meant Miami Beach. That was the closest thing to a city I would consider living in.
Boston. Red Sox, didn’t even have to think about it. Though I lived there before and it was very expensive, traffic was awful, and T fares have gone up a ton since I lived there… Shortest distance to Fenway is to live near it. I may be temporarily transplanted, but I’m a New Englander, damn it! Oh yeah. Great Italian food, a ton of history, and a lotta cultah, too!
I said San Antonio, because it’s slightly closer to my family(Houston) than Dallas, and quite a bit closer to my in-laws (Austin).
Plus, it’s a pretty cool place in it’s own right, and where I was born.
Outside of that, Boston would be nice, and so would San Francisco/Bay Area. I could dig living 30-45 minutes outside Atlanta, but I don’t know about within the city itself.
Well like I said, it wasn’t based strictly on city size - but they are all in the top 30ish (pops over ~400k). I already had 3 cities from California (SF, LA, and SD) so I thought that was enough. Sorry I couldn’t represent everyone’s favorite big city.
I’m pretty happy in Atlanta right now, so I went with it.
If I had to pick a different one, it’d be Chicago, followed by Boston. Having left Tucson last summer and knowing how bad the desert was for me health-wise, anyplace dry and dusty is out. I’ve turned down an opportunity in NYC once - visiting it, I realized it was NOT the right place for me in any way - I’d be miserable living there, though I enjoy visiting.
I agree that it’s too big, but the others on the list are too far away from home. 
Denver. Best city I ever lived in, and I lived in a lot of them.
Then move to Forks. The dreariest place in the lower 48.
Me, I would move to NY in a minute. I grew up in Philly and you’d be amazed how little the Wissahickon park is used. One thing is a major highway (the west river drive, not to mention the Schuylkill parking lot (oh Expressway, sorry) blocks the park from the river.
My brother loved NYC. He lived there for 40 years.
But I hate winter. So Maybe Miami.
I loved Seattle and I loved Boston, but I think I’d pick Seattle because it seemed more laid-back.
If I were picking a city, I’d pick the one I know best - Houston. Which really should be on the list. It’s the fourth largest city in the country.
But with that choice unavailable, I picked the city I knew best on the list - New York. Realistically I wouldn’t want to live there on the standard of living I could afford but the OP covered that point.