Well, if he leaves his job and comes to Canada, you're still `suddenly' uninsured. Being uninsured could actually be problematic in entering Canada anyway. If the border officers finds out that you are visiting Canada without medical insurance, that could certainly be reason for denying entry, since if you needed treatment it would be at the expense of the people of Canada. I'm not judging, or trying to be negative...just alerting you to a real possibility.