Re: shipping a boat. how much?
A couple more thoughts. The Great Lakes also border Canada.
If you could give an idea what boats you are looking at, perhaps I could find some help.
I spend most of my on line time on BOC (Bayliner Owners Club). We have a lot of members in the Great Lakes area and many would be willing to take a non professional look at something you might be interested in.
It wouldn't have to be a Bay. Most are helpful there. I could ask or you could post there. We have non Bay members that haven't saw the light yet.

Or if this carries over til spring, I could swing by on my way to Northern Michigan.
Georgian Bay, a part of Lake Huron is all Canadian waters. Also North Channel which is upper Lake Huron is Canadian. The East shore of Lake Huron is Canadian as is much of Lake Erie. Also parts of Lake Ontario. The prices won't be as good but the Canadian taxes will have been paid.
Winsor Ontario is across the River from Detroit and is also auto country. I know a BOC member who just retired from Ford and may be able to provide some info.
The real buys, I think, will be in the auto areas.
Just one more thing. You may be able to find somethng up to 28' or so on a trailer.
Doug