I have a friend who recently got on with Westjet after about ten years of work. He started out as an instructor (I was one of his students), and through that he met the right people to move up. Unfortunately, in Canada it's as much about knowing the right and being in the right place at the right time as the number of hours. In my ffiend's case this is exactly what happened. He knew the right people, they remembered him when an opening came and asked him to apply. Another point though is that everyone gets there a different way and you have to a route that works for you.
Joining the military in Canada may not be a very good way to get into the airlines here at all. Something half of our air force is made up of helicopters, so while you may get lots of hours on them, it won't apply much to an airliner. I looked at it a couple of years ago, and at that point chances were good that you would end up flying a helicopter. Maybe it's changed, but then they are constantly cutting back the number of fixed wing aircraft.
goates