Used to live across the river in Vancouver WA. Was back two years ago for a visit and the traffic and homeless is a major negative. Saying the traffic isn't as bad as Seattle is not a badge of pride. The homeless always was an issue but it has exploded over the years. Its bad. If you don't like 300+ days of clouds or suffer from SAD then its not the place for you. Otherwise you get used to cloud muted gloom.
Positives. Good coffee shops/stands virtually every corner. Powells Bookstore. Temperate weather for the most part. Access to mountains and the coast within fifty miles either direction. Beautiful greenery everywhere. Great bakery/bagel shops, tons of brew pubs, some really cool areas like 23rd street or movie houses like the Bagdad or the Mission Theater.
It is a great city in certain areas and for specific things. The public transportation is clean and roomy and if you live or work on the line it is a huge advantage. I absolutely hated the traffic but forgot till I visited and got stuck in a six hour jam trying to go over the bridge. Complete stop that is less than a fifteen minute commute, maddening. Sitting stuck in Portland for six hours not moving you really notice the homeless issue.
I moved from Colorado where their is over 300 days of the year of sunshine and dry arid landscape so the first thing I noticed was how green everything was but those clouds are gloomy. The kicker was the traffic, forgot how much I despised that gawd awful traffic. Not for me but I can see how it would be a fit if you settle in the right area and don't have to daily deal with traffic or homeless.