Getting to the root of your first question, the CRTC deems that any media delivered to residents of Canada (i.e. on Canadian soil) is within their jurisdiction. I believe most regulatory bodies operate on similar "boundaries" (e.g. United States FCC), other than maritime bodies that need to delineate a 12-mile radius from their coastline to make the distinction between "territorial" vs. "international" waters[3].
EDIT: If you happen to stream content to a private audience, I think you'd be exempt just because you're too small of a target to go after. But if you tried to scale your Canadian streaming operation up, you'll probably run afoul of the CRTC without obtaining either a license or at least applying for an exemption. IANAL.
[1] http://www.crtc.gc.ca/eng/archive/1999/PB99-197.htm
[2] https://en.wikipedia.org/wiki/Canadian_Radio-television_and_...