I've looked into the "RUM" bike vs "MC" insurance thing and it seems transport Canada is really cracking down on converted off road bikes for street use. Even 'grandfathering' them once they have already been registered won't work. All those converted off road bikes you see on Craigslist or where ever probably won't be re-registered under a new owner.
To go even further, street legal Husabergs and GasGas' are not actually street legal in Canada because they say "Competition Use" on the badge. I was really looking at getting a GasGas 300 two stroke and plating it but its not going to happen. It has to say "MC" on the badge or it doesn't get a plate.
So it seems we are stuck paying $10k for a KTM or Husky, or being stuck with some pseudo off road Japanese DS bike.