OP, despite this sentence here, I would not suggest ruling out Boston. It is my city, and I love it ardently.
Now it’s true that the greatest drawback is the cost of living, but honestly our state minimum wage is higher than federal and if you can find a job in the city, starting pay is often higher than that. Enough to make a living, if you don’t mind roommates. And besides that, if you live and work in the city or some of the nearby areas (Quincy, for example) you can live completely without a car. So yeah, you’ll pay a lot for rent, but $70 a month will get you a T pass. Stack that up against car payments, insurance, gas, maintenance, etc. And it’s one of the most walkable cities in the country. Trust me, you won’t even miss having one.
I live in Dorchester which has some very rough spots and gets a bad rap, but there are plenty of nice neighborhoods that are safe and not too terribly pricey. Same for Southie.
As for food service jobs, we have six or so Whole Foods with great prepared foods departments within easy commuting distance. The pay scale, chances for advancement, and benefits with the company are fantastic. Plus you learn about food constantly and get all sorts of free goodies. (yes, I work for them though not that department and I ardently love my job too.)
In terms of arts, culture, music, history, education - we’ve got it all. You will never be bored. Especially if you like history. Boston is the cradle of the American Revolution after all (Sam Adams’ words, not mine. …well, okay. that one is Fanueil Hall is the cradle of liberty. :))
And we aren’t an outwardly friendly people, no. But as far as being gay, atheist, or whatever else, there’s few places better. Both in the fact that people will stay out of your business, and in terms of the law. This city is very progressive.
Can’t help you about the cold. 