If money is not a problem, which means that you can afford to do and have what you want, where would you want to live? What are the reasons of your choice of that place? Is it the place per se that attract you, or is it you believe that people in such place are nicer?
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There are many beautiful places with varied weathers to fit individual needs. There is some sort of "magical feelings" when living in an island.
Actually, a place is just secondary to being close to love ones when choosing where to live. I agree with you.
Any particular island? An island is a wonderful setting for a "dream paradise".
Italy is really a beautiful inspirational sight for painters.
When your objective to live in a place is to do business then you may be required to stay in a place for a longer time; but it also depends on what business you intend to do.