Are you going to build boats and trailers or just build the boats? What size of boats or trailers? These will affect the requirements. I would start by talking to a nav. arch. as well as Transport Canada Marine Safety and the Coast Guard if you are going to build boats. If you are just building trailers your provincial Department of Transportation will have all the rules and requirements for trailers.
Regardless of whether you are building boats or trailers you may want to look into CSA W47.1 and W47.2 certification for your company, it will help and may be a requirement. As for red tape it will depend what province you are in and the size of the trailers and boats.
Sean