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I'd go with Portland. Portland has tourists sites, busy downtown, lower costs than Seattle and 2.6 million people. There are homeless people here but they don't go knocking on doors. You just have to be careful walking in downtown. There are observation decks on our building. Portland also has great escapes. If you drive an hour in any direction you are on the beach, mountains, rainforests, or a desert. That is why I think you should go to Portland
I don't know, if your a libertarian you really shouldn't live in those cities since they're both very hipster. I'd suggest that you move to a more mainstream city like Chicago or New York City.