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If you look at my personal website toward the bottom of the first page are photographs of the transom area of my 17 foot 1984 Montauk. The boat floats with the motor well drains right at the water line. You can see that where the water marks are on the before paint pictures. I really don't know if there is any water in my hull and I don't know where the water line was when it was new. With older whalers it isn't a matter of if there is water in there but , how much. Maybe you can find some pictures of other whalers to compare to your boat but if it floats ok with the drains above the water I wouldn't worry at all.