Of course it's doable. Anything is doable. But I've seen too many friends who all fantasied about going to NYC right after graduation and ended up with low paying sucky jobs living in lousy housing with poor quality of life, yet they don't understand why they are unhappy. They thought being in NYC is everything, but still feeling unhappy.....
Portland is kinda new hip place for young people. Lot's of creative industries around. However, that's where everyone flocks to. Unless you don't mind working as a waiter at an organic taco stand, or as a bartender at an organic micro brewery, or as a part time staff at an organic bike shop.... good jobs don't come very often because they are taken by much more experienced and competitive people. Of course, no one's stopping you from living off the streets while you figure out what to do with your life. You will probably find many buddies while at it.
For me, one key to being competitive, other than the talent and skills you already have, is being flexible and mobile. You go to where the job is, not go to some lala land and wait for something to happen. I found my official first job in Aug 2008, just before the automotive industry went belly up. I moved more than 700 miles for the job. One year later, my job was not secured anymore, so I found another job 700 miles away at the end of 2009, when the economy crisis really hit the country. People are amazed by how I can "just find a job", but it's more than "just". You got to know what you want, what's important in your life and make necessary sacrifices. To me, this is the time when you don't dream about fancy jobs or career. This is the time when you find something that doesn't make you miserable and save everything you make.
My current job makes me miserable but at least I get to save quite a bit. When better times comes, I am more than ready to pounce.
Having a family is totally different. I can't speak for that myself, but definitely feel the challenge as many of my friends are dealing with it.