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If he's got a job already lined up then Pittsburgh will be a better place to get established, build up a nest egg and then move up to a more pricey area like the Hartford metro area. Wish I had done that instead of staying the Hartford area until I was 28 years old.
Maybe you should visit both cities for about a week, read the local paper and watch the news to see what everything is like, explore a lot of the places that look good to you and the places you could afford and then Decide.
And if that doesn't work out for you...................
My point was that for similar cities, Hartford's streets are either crime ridden and inexpensive or beautiful and pricey. There's very little in between.
Pittsburgh has incredibly affordable housing and even though it lacks Hartford's prime location, it is ideal for a 20 something starting out. Once $$ is saved, the OP would have a much easier time moving to Hartford should he decide to go through with a same-sex marriage.
Connecticut is not an easy place for your average middle income earner, even the most affordable parts which include Hartford and Northeastern CT (quiet corner).
I used to spend hours in the library studying the crime stats from the official FBI books and the city of Pittsburgh and its metro area was always one of the safest million plus metro areas. While the city of Hartford is pretty bad the metro area as a whole is quite safe just like the Pittsburgh metro area.
I would go with Pittsburgh if it was me. As to the "isolation" thing, I've never understood why so many people are concerned with that. I'd rather live in a full service, convenient city that has all the big city amenities you need right then and there than be just a point on the "BosWash Megalopolis" that happens to be "close" to other big cities. Isolation-- being a big blob in the middle of nowhere-- is actually a good thing-- it helps create more of a unique hometown feel even extending to the suburbs. It also means you have better access to some incredible rural and wilderness country. And Pittsburgh is not really that isolated. Then again, I'm from Denver (and will be going back there), where the nearest city of over a million people is an 8-10 hour drive away. Also, if you were to invent some kind of "city per dollar" metric illustrating how much a city offers compared to the cost of living there, Pittsburgh would pack in quite a punch, probably one of the best values out there for an eastern US city.
Pittsburgh, isolated? Hardly. You want isolated then try Comaha and Kansas City. Both cities are on the edge of nowhere. And as Vegaspilgrim pointed out Denver is even more remote as far as its proximity to million markets is concerned.
I have lived in both Hartford and Pittsburgh. They both have their crime areas that are not good by a long shot, but they both have their suburbs that are not too far away from the city that is a comfortable commute. Like someone said though it's cheaper to live in Pittsburgh. You get a better financial head start. I think the next thing you should look at is the clientele and what industries you would like to focus on in each city. ie. Hartford is heavy in insurance clients.
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