I understand your frustrations with silly regulations.
My understanding of the laws in Ontario is that any trailer over 10000 pounds requires a class A license, the same one required for the largest tractor trailer combinations on the road, regardless of the towing vehicle. Also, I believe that in the strictest legal sense the weight of such a trailer has to be included in the weight of the towing vehicle for registration/taxation purposes (actually any trailer of greater than about 7000 pounds, it's not defined by trailer GVWR). In turn, this will make the towing vehicle subject to the CVOR (Commercial Vehicle Operators Regisatration) system which makes the operator subject to daily inspection and duty hours logging. There are some exemptions to the CVOR rules to permit personal use of the vehicle, for example to go home after work. I have registered my truck to avoid the CVOR and my trailer is light enough to only just avoid having to include the weight.
Having said all of this, there are many people in Ontario who operate pickup trucks with heavy trailers without complying with the rules as I understand them, apparently without consequence.
I think there is also an exemption for travel trailers that leaves us with the ludicrous situation that a pickup towing a 16000 pound 5th wheel travel trailer is treated like a car for licensing of the vehicle and driver, but the same pickup towing a 16000 pound 5th wheel flatbed (with a carrier or other CMP) is treated like a large commercial A-train semi trailer rig.
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