Manitoba bike insurance may make up your mind for you.
It has only 1 dividing point, either the bike's under 500cc, or it's over 500cc.
Motorcycle insurance is so high there, I would never
even consider living there again! (5X higher than I pay here)
You can get an online quote here : http://www.mpi.mb.ca/
I think there is quite a difference, so you might be better off with the 250...
Best of luck!