Amazon.ca does not provide support nor sell Kindles. You'll have to use Amazon.com. The short answer is Amazon.com has different prices for sometimes identical merchandise in different regions. Canadians pay $2 per title for (non-optional) wireless delivery.
If you log in to Amazon.com, with your Canadian account info, Amazon filters what you can buy (and often, but not always) what you can see for sale. In that mode, the price you see already has the $2 baked in.
Newspapers and magazine are stripped of all images and tables; but then again, the Kindle DX is not currently sold to a Canadian account.
If you create an order there is no free shipping for a Kindle. Amazon.com does not ship anything free to Canada.
Barnes and Noble will not sell a Nook in Canada either.
Whispernet works in 100 countries around the world. I used it last week on the Pacific coast of Mexico. It will work in Halifax for sure; it uses 3G and can call back to GSM (Rogers is the rumoured partner for AT&T for Amazon).
The Kindle 2 works really well as described on Amazon.com provided you make note of the non-US configuration (like no web browsing, but wikipedia works). With the leather case (highly recommended), international shipping, taxes and exchange, the US$259 works out to abt Can$350.
www.kindle.com has very clear info -- click on the link on the main page "Live Outside the U.S.?" and select Canada.