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1.) As a Canadian, you can download and buy books via WhisperNet without issue or additonal cost. And if you have a WiFi connection available, you can use it as well. Keep in mind, however, that the 3G+WiFi model is the $189 model. The cheaper models are WiFi only, no 3G.
2.) Download via WhisperNet is fast. Very fast.
3.) You are not restricted to Amazon to buy books. I buy from Chapters via Kobo all the time. It does require using a computer as an intermediary, but it's trivially easy. DRM removal of purchased books for personal use and format shifting is legal in Canada.
4.) No screen is better than Kindle's. The current generation of Sony is equal, though I've heard the fonts aren't quite as good. Not sure how easy it is to change fonts/screensavers, etc. on the Sony, but trivial on the Kindle.
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