I am thinking of purchasing a boat in Canada. The boat was manufactured in the US. Is it worth the hassel?

I did the same thing years ago (Before 9-11) and it really was not a hassel. I called and since the boat was built in the states you do not have to pay duty (it was done when shipped to Canada).
When I called about the Duty fee's they gave me a number to call for inspection when returning to the states with the boat (no trailer, so I drove it accross to my marina).

When I got the boat to my marina I called the number and they just asked a few questions and then I was good to go.

I'm not sure about now (after 9-11), but that was my experience.

I am min Canada and sold a boat to US citizen this winter. I towed the boat over the border, and the buyer and I met with a customs officer. He went out and looked at the boat, said he thought the sale price was reasonable and then filled out a form. The only kicker was the emissions. He was anxious to ensure that the 496HO had the emissions sticker on it. Took all of ten minutes (after waiting in line behind a woman who was trying to import chinese art claimed to be worth 100$, but proved by internet search by customs officer to be actually worth 500k.) She got turned around and pointed north.

Have him bring it over for repair pay for it and take it home. Made in the USA done deal.