I found the answer. Turns out the local OPP detachment had the same question, and they recently received clarification from MTO. Both quotes are correct and not conflicting , my pick up truck is considered a commercial vehicle (black plate) for the purpose of this regulation. Hope this helps others.

I am trying to figure out if I can legally pull 2 trailers (a small camper and a 12ft boat) with my pick up truck (I would be under 23m and not over my GVWR, I have tow mirrors and can see both trailers) . I have found 2 (seemingly) conflicting references from mot.gov.on.ca. I will travelling on HWY...