So yeah holy shit, Game Pass Ultimate is bonkers. I just upgraded and confirmed with Xbox that it's one roll up monthly charge of $16.99 CDN. Buuuuut since I was already paying $13.99 for Game Pass, and had prepaid a year of Xbox Live ($6/month) until Feb 2020, they won't start billing until whatever prepaid Live time you had left. So I pay nothing until March 2020 and get it all. AND instead of $13.99 and about $6 a month, it's a flat $16.99 too. Dang.