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I lived in the NH seacoast for quite some time. Portsmouth is a great town, but it is expensive. I currently live in Portland. You can't go wrong with either town. Portland will provide the big city feel, but is still completely walkable, affordable (for the most part), and safe (again, for the most part). Portsmouth is a little art town with many deep pocketed residents. This is reflected in the price of many things like housing, food, entertainment, etc. Both towns can be done on a budget, but Portland has more free entertainment. Then again, NH has no income tax.
To show you how hard this choice can be,
-I lived in Portland from 2000-2002
-then Durham, Newmarket, and Dover (all close towns to Portsmouth) from 2002-2005
-then back to Portland from 2005-2006
-then back to Newmarket from 2006-2008
-and now I'm back in Portland
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