Theory: An accurate description of a city can be extrapolated by observing how locals behave in the street.
In Portland, the pedestrian in the street is sacred. Bikes and pedestrians are pretty much honored and respected. I never see anyone in a rush. Everyone just lets each other go along. No hurry man, it's all good, your carbon footprint is lower than mine so just go along and take your time crossing the street.
This has caused me, and the drivers of Portland, a great deal of stress. I am from a city where drivers speed up if they see a pedestrian crossing the street. Here I am forever darting in and out of the street as I am used to doing in Chicago. In my mind, it's every man for himself, and the pedestrian is the lowest on the street hierarchy, not the top. Sometimes I'll just find myself jaywalking across the street with my zigzag anti-getting-hit-by-car plan all in place, and everyone just stops, and then I stop and we're all just frozen in the street and if they'd just stop respecting me we could all get along.
And here the peds respect the drivers too. I'll be walking with my friends, locals, and all of sudden I look around and they're not there. They've stopped minutes ago at the stop light even though there's no cars in the street.
I know, I know. I need to play by the rules...but it's definitely one of the hardest behaviors to change, and one that makes me stick out as a non-local, or just an asshole. Play by the rules, respect each other, and most importantly, deserve the respect others give you.