Why can't I watch web-based video in Canada?

It has nothing to do with an advantage to a company of not having Canadians watch US programming, it is completely based on Copyright owners, which is MUCH more complicated than I could have imagined.

For instance, you'd think that because Comedy Central broadcasts the Daily Show, they would have the rights to distribute that show online in all countries, but The production company of The Daily Show, provides only the rights to broadcast the show in the US.

This way, the producers get to sell the same show again in a different region. If Comedy Central were permitted to broadcast beyond US borders, it would limit the amount the producers could make on the show.

I believe it has has less to do with advertising to the consumer, which is revenue to the broadcast company, and more about the revenue to the production company, which is paid by the broadcaster.

If we end up in an environment where you pay directly for content, this would probably change, as you'd possibly be paying directly to the production company and cut out the middle man. But I suspect that is all a long way off.