I've imported quite a few into Ontario as I used to have a small business selling fishing boats many years ago. The boat in my avatar came from Lake George. It is a very simple process for coming from the US to Canada and it cannot be too complicated the other way. It is as simple as claiming an item you bought in the US along with having the titles/registration from the owner, a bill of sale, a copy of the ad, and you have to ensure that there are no recalls on the trailer prior to importation. Also the trailer label must be legible such that the VIN and month/year the trailer was built is readable.
Sounds like a lot? Not really, it is all basic stuff. There is some stuff behind the scenes that is required for someone to ensure that there are no liens owing but beyond that, simple. For someone who has not done this before, it may seem a bit daunting but it truly is not.
I get it - too complicated for some. That is fine.
For those willing to take on this task, I'd be willing to better the price just before I store it. Only selling because of personal matters otherwise it would be slipped on the north shore next year.