When I moved down to South Carolina from Alberta I had to import my truck & flatbed trailer.
I used a company from Lethbridge, AB who specializes at doing this.
It cost me $500.00 per unit and a lady from the importing company had to meet me before I went to the border to verify that each vehicle met all US safety standards and to take some pictures to verify this. She set everything up with the customs broker and it was painless at the border. One thing that's very important to remember is that even if the trailer was manufactured in the US and sold new in Canada you still have to pay Excise Tax in the US. No one at US Customs will tell you this it's something you have to do on your own.