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Lake Ontario vs Lake Michigan
Living close to the boat would be a plus. It''s the best way to go. Living far away sucks.
Sorry for the news but having lived near Ontario I can tell you the eastern shore can be quite wild. I have seen 25 ft breakers crash ashore in heavy weather. The shallow depth kicks up some real weather from time to time. Ontario is every bit the danger as Michigan. The only lake that really has much of a difference is Superior -it''s very dangerous and the cold water deadly. Clearly the most serious of the great lakes. The Great Lakes deserve all the respect of a great ocean - even the smaller ones.
From Ontario you can get to Albany via the NYS Barge Canal entering at Oswego or Buffalo. You''ll need to step the mast to get there (21 ft clearence) howvever there can be assitance at both ends as it is done quite a bit. Very pretty trip! The great circle can be accessed via Chicago so you can''t really get there without going back though the other lakes.