Ok Rob I'm going to throw my in. You have to call the MTO and find out what they will let you tow. In Ontario, if you are over a certain total weight you need and "A" licence. You will probably need a yellow sticker on both the truck and trailer and a yearly safety inspection on the truck. With that yellow sticker you also need to pay more for the licence plate sticker. You will probably have to keep a log book too.

The suggestion of a motorhome will save you from all this grief for now but the rumor is that they are going to come out with new legislation to impose the same type of rules on motorhomes too.

My best advice is to go down to the MTO office and find out what you will be reqired to have to tow. They do road side checks on the way to the track and the will fine the crap out of you if you are not right.
Steve