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Portland by far. It is simply not possible for a mid-western city to be as cool as a west coast city.
I want to say that was supposed to be sarcasm, but I wonder if you actually are that naive.
My brother-in-law who moved to Minneapolis from Santa Cruz specifically for the arts scene (and also the bicycle culture) would highly disagree with you. Minneapolis and Portland are on pretty even footing when it comes to attracting young and educated people seeking urban lifestyles. If you want to say Portland is preferable because you like a milder climate, then that's perfectly reasonable, but it's certainly not "cooler". I suggest you do some traveling before making inane, sweeping claims about places you've never even been.
You're saying the equivalent of "LA is cooler than Portland" or "NYC is cooler than Boston" or "Toronto is cooler than Montreal." It's meaningless and mega subjective, of course possible can and will disagree with that.
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