Hmm, after some more research it seems my biggest problem is not that I haven't had a Canadian license for very long but that I've never been insured (in Canada or elsewhere).
On the bright side, TD Home&Auto has a discount deal with the company I work for, so I'll get away with significantly less than $400 (Canadian) a month for full coverage. Slightly below my excruciating pain threshold, but still not great.
