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I'm off-topic, but if I were to pick a place to spend the winter it would be somewhere south of the border, where my dollars would go farther and I'd enjoy getting to know a different culture.
If narrowed down to cities then Flagstaff, Santa Fe, San Diego, Los Angeles, San Francisco, or preferably somewhere along the central coast of California like Monterey. Tucson does have pleasant winters but Flagstaff actually gets snow and is just as pleasant in the long run.
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