not sure if this idea of using a US insurance company is for "premium " savings, but if that's the reasoning then wouldn't it be a easier idea to get insurance from Alberta, as the motorcycle insurance premiums are half of what Ontario residents pay.
Example ,My bike : Kawasaki zx10r, basic coverage, no collision here {Ontario}, $1100. Same bike with full coverage, Alberta price $390 per year.
And they insure any age , 17 year old with GSXR1000 pays less than $1000 per year, no motorcycle experience , new rider Alberta rates are more than half of what we pay in Ontario