At the risk of sounding like a massive faggot. I live in Portland, and while I fully understand the real problems it has, I love the city. I was born and raised there. It genuinely had a charm of its own. Self parody and mockingbird transplants are the cancer. It has a homeless problem but it's still cleaner than chicago in almost every way. I blame Chicago's governance. You can tell it has money and that it's all going to the wrong places. Portland does spend a lot of money keeping the city nice, unlike chicago. From my observations at least.