However, the unattractive size of the Canadian market is offset by the similarity of Canadian customers to their US counterparts (largely the same culture, values, language), and the country’s proximity to the US.

That said, there are still barriers to entering the Canadian market. It’s a different country, and there are different laws – companies usually need to set up a separate company to comply with Canadian laws. Most content licenses are negotiated on a per-country or region basis, and so entering the Canadian market with a content-based product (Hulu, for example) requires negotiating the Canadian rights. Different laws also mean that certain regulated technologies may not yet be available in Canada due to the relative sluggishness of the regulatory infrastructure (CRTC, I’m looking at you).

All of these little differences introduce friction into the system, something that will slow a company’s ability to roll out its products to a new geography. As a company with limited resources, you’re more likely to want to enter a big market with minimal barriers, than a small one. So companies make the logical choice: they put off entering Canada, and may even introduce products in Europe instead (really large market, slightly higher barriers than Canada, so a better return on investment overall).

My response is “let’s make a deal”: if they launch services simultaneously in Canada, with the same pricing and options, then we can talk.

Here’s another one that drives me crazy, but it’s from the other side of the border: The $%&^# Patriot Act. It effectively means that there are few (if any) ‘Cloud services’ or development of such in Canada. If you do work in any sensitive areas for privacy (like Medical Records, Government work, etc.), there is no option to use Google anything or Amazon’s application services. So the old models are still in effect and Canada is left behind technologically.

I’ve written about this before, but if anything, the problem has gotten worse; Despite being ‘The Most Wired Country on Earth’ *per capita*, eccommerce is incredibly expensive here. There is, as you say, no Amazon equivalent, and relatively poor options for online shopping (especially factoring in the shipping costs). Having no reasonably priced streaming movie service (or TV like Hulu) means that Canadians essentially have become the biggest users of bittorrent in North America. Great, we’re the best pirates around thanks to corporations painting us into a corner.

Again, even though there are ways to get a US iTunes account to hack around this problem, that’s not the point. I shouldn’t have to tunnel under these pointless digital fences…it’s the goddamn 21st century. The whole point of the net is to remove barriers.