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I am in Michigan and I bought my boat in Florida.
The worst condition boat I looked at, by far (among about 50+) was on Lake Michigan. The premiums asked for good boats on the lakes was over my budget. there are a lot of derelict boats around here. True, one hurricane can totally destroy a boat. But years of sitting out uncovered in the winter can also make a real mess of decks. As soon as you have some water leaks, the freeze/thaw/freeze/thaw cycle will make a real mess. And all the unemployed cut back first on maintenance. I go to my boat all winter long and see plenty of boats totally uncovered and caked in ice. Ice that gets into the scuppers and expands and cracks the scupper, etc. Masts leak water into the bilge and the water freezes and makes a mess of bilge pumps, stringers, wiring, hoses, etc.
So you need to decide what kind of boat you want, what amount of work you are willing to put into it and then search everywhere until you find the RIGHT boat. Since you are prepared to transport, then don't limit yourself to one area.
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