Over the years I have heard of several people on several different islands staying the winter..... Most have had hover crafts, once or twice airboats... I do recall someone one time claiming to have done it with out either, and just had to be patient and supplied while the ice formed.
With a good generator, and sufficient food supplies, anything is achievable. People live remotely in Alaska as a way of life.
To me the biggest risk, is making sure that the town your island resides in has emergancy equipment that can get to you... Saying you got sick and died because emergency services couldn't get to you in the Alaska wilderness is understandable, on Lake Winnipesaukee, it would be considered poor planning.
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Life is about how much time you can spend relaxing... I do it on an island that isn't really an island.....
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