Edited: I called Air Canada and while I'm not fully satisfied, my urge to make someone's head roll has dissipated. (tidbit of advice: many national call centres are in Montréal, if you can speak French, you tend to get better service) Rather than strike the entire original entry I have erased the bulk of it.
So to make a long story short, Skylar and I will now both leave together at 8. As for my flight leaving from San Fran, it's back to its original departure time. They had moved it up FOURTEEN hours. WTF Air Canada? 9 months I've been planning this trip. Don't fuck with my travelling plans, nothing good will come of that, ever.