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Personally, I'd say maintain accounts for both countries, for maximum selection/pricing advantage.
Even in the Amazon store, books can sometimes be a lot cheaper for Canadians because Agency pricing doesn't apply up here and thus Amazon is free to discount titles across the board, which they occasionally do. Same thing at Kobo, where coupons can be applied to books up here that won't work down in the States (and you'd have to jump through hoops with an IP proxy to buy as a "US" Kobo customer from Canada anyway).
Plus we have access to (mostly Canadian and sometimes UK-authored) books that other countries don't. Geo-restrictions work both ways.
Also, you may want to go and download the official user manuals for any readers you're interested in, to get an idea of exactly what features they officially support.
The people in the forums here are great when it comes to user experience and tips and tricks, but sometimes some of the more obscure things you can do get glossed over because nobody reads the manual and most people just haven't come across it during typical usage.
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