Since your voyage is originating in WI I can say that in WI your boat is considered a vehicle. However its not WI laws that you need to be worried about.
Bear in mind that even if you're in the People's Republic of New York they still don't have the right to board and seize unless they have reasonable suspicion. Keep your nose clean and you should be ok but then I'm no expert on this so I could be VERY wrong.
Canada could be sticky but you seem to already know more about that than I do.
This is who we are, what we do.