If you’re a leftist/communist/fascist (but I repeat myself), Portland is a good choice for your protest. Because you know that the mayor and the police won’t just be neutral. They’ll be on your side.
On the other hand, if you’re a conservative, protesting in Portland is rather gutsy.
I was walking around Portland a couple of years ago and stumbled across a lunch room called something like "The People's Sandwich Shop". Their logo was a didactic poster reminiscent of Mao's cultural revolution, and NOT even tongue-in-cheek.
I thought how weird that a business would in embrace communism, and adopt a communist inspired theme for their company logo. "Forget it Jake. It's Portlandtown.".
I had a good laugh earlier this year when a famous feminist bookstore in Portland went out of business because there weren't enough volunteers to run it. I thought, what a great business plan—find volunteer employees who will work for free! Somehow that didn't quite work out.