I lived there for 6 months. There is basically zero chance you can expect any type of income from the place between Novmeber - May. The population of ths island is about 140000, but will boom to about over 1M in summer - so there is a HUGE overcapacity of winter homes to rent.
And the area around Cavendish is likely the nicest, but I am not really sure. I do know that is the tourist hotspot.
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