There's two parts to your question: the DirecTV part, and the TiVo part.
Part 1: DirecTV. I'll bet that DirecTV would love to sell service to the Canucks, but the issue there is that they aren't allowed by the Canadian government. The Canadian version of the FCC has some pretty keen ideas about keeping Canadians watching Canadian content. If DirecTV were to provide service, they couldn't just sell the same service they sell to the Merkins. They'd have to sell a special version of the service that was at least a certain percentage of Canadian content (some Canadian can surely jump in here with actual numbers). However, my guess would be that they still wouldn't be allowed to sell into that market because the Canadian FCC (CRTC?) has already issued licenses for Canadian companies to do direct broadcast satellite services, and since they're so very territorial and protectionist...
As far as the TiVo thing goes, that one seems like a case of limited resources, and not wanting to expend them on a little market like the Great White North, since selling into Canada would require a lot of up front costs like setting up sales and distribution deals, finding a good source for guide data for all that aforementioned Canadian programming, etc.
Of course, this is all my ignorant American perspective. I've only spent a grand total of a few hours in Canada, so an actual Canadian might be able to shed some more light on the subject.
As far as Alaska and Hawaii, I remember something about one of those states petitioning the FCC to not renew a license for one of the DBS companies unless they would start providing the same service there that they did to the continental US. Seems that they forgot that the planet's round. I do know that at least one of the DBS companies has a separate bird pointing at Hawaii to offer some limited service, and I've heard tales of Alaskans with really big dishes pointed at the horizon to get their signals.
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-Aaron