You seem to have received quite a variety of answers!
Okay, here is the gist on Portland.
I recently had to move back to San Francisco, where I am from, and am counting the days until I make my way back to Portland, Oregon. It is, in my opinion, the best city on the west coast.
However, that's only my opinion, and we (obviously) are not the same person.
Like anything it depends on what you're interested in. For example, I'm a 32 year old female who is creative and likes things a little ... different. As the motto says, "Keep Portland Weird", and what a fitting motto indeed. My hair is a mixture of pinks, blues and greens, and while it may cause more than one eyebrow to raise in other cities, it's barely even noticed in Portland. Everyone is a little punk rock in Portland. It's what makes the city so killer.
For instance:
Oregon has the most liberal free speech laws in the country, and because of this Portland boasts the most strip clubs per capita in the nation. The Bar Fly bus even does a tour of nudie bars, complete with discounted entry fees and lap dances.
Portland has more micro-breweries than anywhere else in the nation.
Portland has more bike commuters in the country (we're bicycle friendly here!)
Portland has the largest independent book store in the world, Powell's Books (the best place on earth).
According to a recent NY-Times article, Portland is the most affordable city on the west coast by a large margin (over 100k!).
If you're into outdoor sports you won't be disappointed either, as snowboarding, rock climbing, surfing, skateboarding, cycling and more are either right outside your door, or a close drive away.
However, all of this being said, the move from NY to PDX will likely come with a few speed bumps. A friend of mine made the same move and likened it to "hitting a wall" as far as his personal life goes. Not for lack of people, but for lack of the same sort of "City that Never Sleeps" lifestyle. Portland rocks, but it's still small. Keep that in mind.
One more thing: it's best to be open minded, queer friendly and art hungry when moving to Portland. It's a creative city with like-minded individuals and they locals would like to keep it that way.
I hope this helps, and remember to try Stumptown coffee when you finally make it to the Great Northwest--it's to die for!