The only thing is that this could be any town USA. Downtown Portland is the coolest. The problem for me is all the shit people pile up in their yards? I guess there are few zone controls. The sprawling grocery stores, and the under belly of the city just sucks. The drug situation, yeah, a lot like Chicago. Never been to Chicago, but I'm glad I missed it.
The majority of the people in PDX are transplants. Just because you've lived here for 10+ years doesn't make you a native either. Before the hipsters gentrified NE PDX and the minorities were pushed out into Gresham or oblivion, PDX actually had a real "hood", black folks and all. Say it ain't so! Don't even get on a so called "transplants" case when the majority of people in PDX are transplants. PDX will be used up just like San Fran, Chicago, Brooklyn, you name it. Parts of Chicago are still "hip" and cool, but PDX is wide open for the taking by everyone else who is burnt out living in the real world...
I just checked craigslist for costs of renting an apartment in Oak Park, a suburb of Chicago that is comparable to inner SE Portland. Oak Park is cheaper than inner SE.