We had a 1000 Islands Airboat at one point and could access the island year round. I found the airboat to be much safer and reliable than hovercrafts. A quick search on this site for airboat in the forums or gallery will bring up pictures of our yellow boat. It was featured in Airboating Magazine at one point.
As long as your place is set up for winter use (proper heat, water, backup generator, etc) the transportation side is not that hard. All it takes is $$$.
If I did not have 3 younger kids with lots of commitments I would live on the islands year round. I am sure I will be back to it at some point.
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