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Actually, with money, it is possible to combine big city, place to raise kids, tropical, and beach house all in one place - Miami comes to mind, maybe some cities in the Caribbean, northern South America, and possibly some cities in southeast Asia -, but adding ski resort to that would be more difficult.
Southern California is nice all year round, southern Florida is particularly pleasant in the winter, but so is the Algarve region of Portugal, I like New York in June as the song says, but most of all I'd say the most beautiful time of the year is September on the northern shores of the Mediterranean, especially Greece, during grape harvest time, long days of golden sun, enough to radiate inebriating warmth, not too much to scorch, I spent carefree days there.
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