Re: Canadian resident registering boat in US. Duty question
I am canadian and sail lake Champlain in NY/VT, owning a canadian registered boat.
I am no expert in the matter but many canadian boaters around us own US registered boats and bring them to the canadian side every winter and are knowned as "inbound" boats. The only draw back is that they have to be back in US water by a certain date (July?) and need to apply for longer stays to perform repairs.
Maybe this works for boats entering and leaving canadian waters through the same custom? May be the OP can check with Transport Canada?
I wonder how long (or short) is the sailing season in Alaska...