Well if you're willing to spend $1,000 I'd suggest buying both, writing a review and then selling the loser. Just kidding.
Things you're interested in comparing:
1. Screen quality (contrast, refresh rate, etc)
They use the same E-Ink Vizplex display from the same supplier (PVI) so this is a wash. I suspect that the difference you're seeing is a result of the white case on the Kindle vs the black case on the Cybook. I haven't actually compared them side by side though. If the pictures of the Cybook had embolden fonts enabled it would compare differently as well.
2. Usability and durability (interface, buttons, ergonomics, etc)
I'm happy with the buttons on the Cybook. I would probably give the edge to the Kindle but it's a personal preference. Durability is hard to answer because neither has been out long enough. I have read complaints about accidentally turning the page on the Kindle and this isn't a problem on the Cybook.
3. Added features, and how good they are
The downloadable fonts and embolden feature are benefits to the Cybook. The dictionary lookup works fine for my needs. The keyboard and wireless access are the big benefits for the Kindle.
4. Content availability-fiction (including hassle and quality)
Finding content hasn't been a problem with the Cybook and I like the ability to purchase from multiple online book stores and shop on price. I personally prefer that Bookeen and iRex have created ebook readers without their own book store and voted with my wallet on this one. I haven't found an instance where Amazon has had an ebook that I wanted to read that wasn't available from other ebook retailers.
5. Anything else you can think of (seriously, I want to hear everything)
Since the Kindle isn't available in Canada I'm not sure if Amazon would honor the warranty directly. You'd probably have to go through your USA friends or a USA supplier. Probably not a concern if you're moving to the states anyway but something I'd personally investigate before purchasing. Hopefully Amazon will announce in Canada and this will be a non issue.
End of the day I think you'd be very happy with either one.