Portland seems like it'd be okay for a day or two if you had money.
Otherwise, it's where all the scumfucks and oogles go to get drunk and shoot heroin. It's a dreary, detestable place where everyone's hatred for one another is exceeded only by their hatred of themselves. Portland is only nice in the summer time, but the aforementioned "traveling kids" completely ruin it, spanging and pretending to busk and generally disrupting everything. I don't know about you, but anywhere that's a destination for "Traveling kids" is not a destination of mine.
Sisters of the Road is a box full of junkies and psychopathic homebums. The Black Rose is actually quite cool, though, and I'm not even an anarchist. Also, there are some really neat cafes around that place, one in particular stands out in my memory but the name escapes me.
in summation, go to PDX and enjoy it for a day or two, then leave.