Hey Matt
Imported a stump grinder on a trailer last year and did some trucks a few years ago. As well purchased a chipper in Ontario and brought it to Quebec.
In Quebec you will have to safety/register and license your chipper unlike Ontario where no license is required. Buying a chipper in Quebec means no safety.
The RIV part is easy (send the money). The info is given at the border and RIV sends you the forms. Canadian Tire is the RIV rep and all they do is check the VIN plate for accuracy against the paperwork and fax it to RIV.
Registering with SAAQ is the hard part. You need a good paper trail. One office wouldn't register the stumper trailer because it was purchased at auction and did not have a document stating the seller authorized the sale. Waited till I had a few things to register went to another SAAQ office and it went through. Often there is no original title when purchased in a state that does not require registration so you need some good proof of ownership and a valid sale document.
Little story. To get the chipper safetied the VIN plate with the GVWR rating was gone so the calculation was done using the rating on the tires. The tires were too good and the calculated GVWR put the chipper/trailer in the range that required brakes, which it didn't have or need since no load would be carried. Had to go buy the lowest rated tires I could find to fit, pass the safety, then take them off and Kijiji for a loss. All with the knowledge of the safety folks. Bureaucracy at its best.
The price has to be right to put up with the headaches. Get a firm shipping price, that can be a deal breaker and you will need a customs broker, less than $200. Then pay your GST and your TVQ because you have to register the darn thing!