Updated
After finally getting thru to MTO enforcement, they have stated that the following is what I am required to have;
1) Do not need a commercial drivers licence as I am not over 24000 lbs total weight
2) Do need to increase the plate weight limit to 21000 lbs
3) Do need a yearly safety inspection of the truck
4) Do not need a yearly safety inspection of the TT
I wish the lady at Service Ontario knew all this, as it would not have had me worrying all weekend long.
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