I've done the reverse a few times, have all of your paperwork dealt with, call the border crossing several times in the weeks leading up as things change daily, get the name of the border person too as that may help if things get iffey. I've had it go super smooth and they've been incredibly helpful but I've also been there for hours being interrogated. The Canadian side is more interested in the trailer as it is what hits the road, they don't really give 2 shakes about the boat. Seems to be a roll of the dice, Good luck!
Canadian side could be starting job action on Friday, might be a long line.