I had a great chat with the YOW concierge agents today and learned a bit about the WiFi on the 737 MAX.
It turns out, AC does intend to make the WiFi plan benefit (75K+) work on the Thales systems on the 737 MAX. They are working to build a "back-end integration" with Aeroplan to add the "Sign in with Aeroplan" option on these aircraft.
Of course, there is no estimated timeline for this yet, but at least we know it's the intention to support it, and it's not going to always be a separate plan/system.