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I've spent at least 6 mo in a lot of cities - Seattle, Portland, Boise, Moscow (idaho), San Diego, Boston, New York, Melbourne - but the dirtiest one by far is San Francisco. Why? Also why so many homeless? I liked homeless people in Seattle; the ones here make me feel unsafe.
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I was there in the winter (stayed in Gangnam!) so maybe it was cleaner? I don't remember seeing a single homeless person. Did see a lot of people vomiting everywhere. Still tho, Seoul winter was waaaay cleaner than SF winter.
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