Overall, in your experience. WLB, TC, atmosphere, etc. Why?
Boston. Manageable city to navigate, some suburbs are reasonably priced. Not too small to be bored
Boston is great. Would totally live there over NYC, given identical TC. It's like the Seattle of the east coast, except much sunnier outside of the summer months. Surrounded by waterways and near nature, with good air quality, beautiful architecture and easy access to nature. Plus great (and clean) public transit, on par with Chicago, SF and D.C. It seems better than Seattle, although the state income tax and icy east coast skiing are major downsides.
SF > NYC if you're athletic, outdoorsy, health conscious and aren't single (and I've lived in both). SF has much better weather, air quality, access to nature and city cleanliness in all but 4 neighborhoods. It's also easier to find healthy food at restaurants in SF at all price points, although variety is admittedly better in NYC. Cost of living for renters in Manhattan and SF is quite similar. NYC's city income tax (and resulting higher effective taxation) is the only drag on savings there as compared to SF.
What did you spend on food/mo in each city, roughly? Just curious.
About the same amount for groceries at Whole Foods. Slightly more in NYC on eating out because in Manhattan, it's tough to find anything I consider passably healthy for less than $12 lunch/$18 dinner (with tax and tip) at restaurants here. Nothing here like the healthy and cheap eateries that fill some SF neighborhoods. I eat out 2-4x per week in both cities. I'm paying about $150 less for rent + utilities in Manhattan than in SF.
Tokyo
Live near Princeton University and work in NYC. Best of both worlds.
Ugh that's a terrible commute. 1.5-2h each way, so 3-4h per day
Yes, but got used to it. Express trains help. 2 hours each way, door-to-door.
Chicago is pretty good, Illinois is an absolute shit though.
San Diego?
Los Angeles. Get out and enjoy the beach
NYC hands down. You only live once
What sort of TC does a couple have to be making to be "comfortable" (not having to pinch pennies)?
If you already have a SO, I'd say SF can be great. A lot of stuff to explore, amazing weather. NYC is really amazing if you're young and single I feel like.