It really does take a different mindset to live on an island (at least one without a bridge to the mainland!). Here on Catalina we are very close to the big city life, but a world away as well.
I've seen many people come and go over the past 35 years here. The idyllic island life of summer here quickly turns into winter where heavy rains may flood us, storms may prevent the barge from bringing food staples (milk, bread, lox) for a few days, you're "stuck" with the same group of people for months on end.
Long-termers here consider a newcomer established if they survive a winter (I prefer to wait through two winters). People actually go get rock fever. Because so many want to live here, wages are low (I know some extremely experienced dive professionals getting $8/hr). Because so many want to live here, housing prices (and rentals IF you can find a year-round one) are very high.
For me the joy of diving so often (~250 dives/year) outweighs most of the drawbacks. I can always take an hour boat ride and have all the sins of the big city to enjoy.
Of course this is southern California and our winters are far from tropical. Has me considering a relocation to a tropical island... perhaps only 6 months of the year!
Dr. Bill