Second question: finding a cool city to settle in - how to choose, how to be adventurous, etc.
In my opinion it's really important to live close to an airport, especially when you are living far from home. I lived 2 hours from an airport at one point and between traveling myself or picking up visitors it was a lot of driving. With gas prices where they are it's important to think about that. Plus after a long flight it was a big pain to then get in your car and drive a few hours. I know a lot of the time my flight would get in at like 9pm and I wouldn't be home until after 11pm.
It must be my journalism background or just common sense, but I research a lot about areas. When you are moving to an new area of the country it's really important to look at cost of living. The cost of living in TX was nearly 52% less expensive than NY...but it's reflected in salary as well. The same goes the other way, it may seem awesome to be making a higher paycheck in a city, but realize everything is more expensive there. Perfect example I was living in a 2 bedroom 2 bathroom 1,000 sq ft apartment and paid $695 a month for it in TX. My sister lives in a studio in Queens and pays $1,000 a month. Making in the $30,000s in TX is doing pretty well...making in the $30,000s in NY is just getting by.
I also am a big fan of Wikipedia - Wiki the city or town you are moving too and then check out the links the references are from. Also go to the town's website and visitor's bureau. Since I work in Higher Education there are at least always things going on at the college - sports, theatre, speakers. But I am lucky enough to now be living in a pretty fun college town with lots to do and see. Plus Atlanta isn't too far. That's along thing, if you live over an hour from a big city it may not be as fun if you don't know people that live there. It's a pain to drive over an hour to do something and then have to turn around and drive back, especially if you wanted to go out to the bars. Having friends in or closer to the city is helpful so you can crash there and will probably increase you going.
Third question: settling in to a cool new city - how to meet people like you, find
good places to hang out, restaurants, etc.
Once in your new city - I suggest looking at craigslist for community events/classes/volunteer opportunities. Also looking at the town's official website, local papers and listening to the local radio stations.
When you're in a new city you need to put yourself out there, my best tool is my accent. Being from New York and living in the south has afforded me the opportunity to be noticed just by talking...and yes some times I lay the accent on a little thick, but it works!
Another way to network in a new city is if you were in a sorority or fraternity in college - contact a local chapter and they will take you under their wing. I joined a sorority AFTER graduating from college - a big plus for doing so was the network I would then be apart of. A bunch sororities will allow you to become an alumni initiate, so look into it if that appeals to you.
Don't disregard religion. I'm not the most religious person in the world and I don't plan to be. But after 12 years of Catholic school and a 5 year hiatus from religion as a whole - I am taking a peek around. Again living in the deep south may be an influence as well - but I find I am more inspired by the level of spirituality here than overwhelmed by it. Lots of folks seem to have a sincere relationship with God and I think that's pretty cool. Either way church is another social outlet where people can be pretty friendly. I can't really speak of the success I had had yet, but as of last week I started exploring different denominations of Christianity. I am going to a different service for a two months or so to see if I like any and then from there hopefully find one that "fits" then get involved and meet folks. So I started my "spiritual journey" with going to an Episcopalian service. Based on what I read about the religion, I felt on paper at least it seemed most in line with my beliefs. I'm really looking for a liberal Christian denomination, but one that still have the tradition type of service with all the pomp and circumstance. I was really surprised how similar the Episcopalian service was to Catholic Mass. The prayers were very similar if not exactly the same. There were more singing and it was a little more laid back that Mass. When it came to the sign of people everyone in the whole church moved around and like shook hands with everyone else. There were only like 60 people there and it was a small church - which was different than Masses I have gone to. So everyone pretty much knew I was a newbie and the Pastor? Reverend? (I still need to learn all the vernacular) made it a point to talk to me. I'm even going to go to a Southern Baptist service - I don't think Baptist is the denomination for me, but I'm curious to check it out, especially since a lot of people I know in Alabama are Baptist. I will be sure to keep you up to date on my religious happenings.
PS - I'm going home to NY next Friday for a few days and I'm super excited!