I have had my summer vacation dates approved at work so I can start the business of making bookings and the like. As luck would have it, there are seat sales on right now with WestJet and Porter so I have already booked flights to Winnipeg and from Sault Ste-Marie with those airlines respectively.
Via Rail is "annoyingly" having a 50% off sale right now which doesn't cover September which is when I will be travelling on it. There is still plenty of time to wait.
In order to gain an authoritative idea as to the logistics of getting off the Canadian in Clearwater, I made an electronic inquiry with Via Rail. I received a clear, positive answer which included plenty of useful information. I will keep a copy the email with me.