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 11/17 for 45km then on a FSR. I found this reference under " Recreational Vehicles " " Towing More Than One Vehicle Cars, passenger vans and SUVs are not permitted to tow more than one trailer or one vehicle. Motor homes, trucks, pickup trucks and truck campers are legally permitted ...