Please forgive me for laughing Sean but eBay Canada is NOT a big part of eBay. eBay Canada is a very small part of the bigger picture. UK & Germany are way bigger than Canada. I think even Australia is bigger than Canada but I'm not certain of that.
It'll NEVER in a million years be held in Canada. The majority of people that go to eBay Live are Americans. The entire thing is geared to Americans. Having it anywhere else makes no sense whatsoever. You'll not only not have people going to the convention you won't have any vendors for it either. They too are for US sellers. Some of whom don't even sell to Canadians. Why would they come here for a convention that's useless for them? USPS is a massive part of eBay & eBay Live. Do you really think they're going to come to Canada for any reason? Not bloody likely.
The very fact that the US dollar isn't strong is reason alone not to take it outside the US. That goes for conventioners as well as vendors. As it is with the economy & the lower dollar, they're getting fewer vendors. Companies aren't willing to spend the money and are being more selective about what conventions they go to. Travelling out of country with all they have to bring is a major hassle & expense.
Not going to happen & don't hold your breath. All you can possibly hope for is some sort of localized convention for Canadians with info geared directly to Canadian eBayers but I doubt that would happen either. They don't have the budget, San Jose probably wouldn't let it happen, there's probably not a lot of interest in it and then you'd get people B&Ming that Toronto isn't the centre of the universe & we won't come if it's held there.
When you find doing what's right hard to do - you've got a problem.