I may not be the best person to answer these, but I'll answer what I can.
1 - I really like pages over files. Pages allows you to edit as needed, use HTML, embed links, videos, and utilize other plugins your school can get, without having to constantly download, edit, and upload files. Many faculty however stick with just files. That does seem to cause more issue with students accessing it, especially on mobile devices.
2 - It takes about the same for equal content.
3 - If you're using hosted Canvas through Instructure, it's extremely reliable. We've had very little downtime - measured in minutes - over the past year.
4 - It's a wiki page. So you can see revisions and who did it, but not simultanous editing like you can with something like a google doc. You can't leave notes directly on the page, however, you can have multiple pages in a course, and some can be visible to students while others are only visible to the instructor(s).
5 - It really depends on what the user wants to do. I often say in training sessions that Canvas has a huge amount of power and a very deep array of tools, but you don't have to use them all. One of the features that I really like that you didn't ask about is Modules, which allows organization in the class. So a student knows exactly what they need to do in what order. So they start their week with a quiz, then know to go to a reading, then to a video, then to a content page, then to an assignment, all without having to hunt through various menus. Instead they just click "Next" at the bottom of the page.
6 - Big sticking point. They're working on it. Instructure spent several years trying to drag faculty into the 21st century and get away from massive stacks of paper, but I think they've finally surrendered the point. They said during instructurecon that being able to print off various parts of the course is coming. Currently you can get an ePub of a course, which isn't as nice, but is printable.
Followup questions
1 - Our population is pretty split. Our last LMS evolved into nothing but file storage, so some faculty are just taking those same files and loading them into Canvas. Others are spending the time to really utilize the tools available to them and make a functional online classroom
2 - see above.
3 - Check out the Canvas Engagement Strategies area for ideas on this. I'm not sure I've seen anything specifically addressing pages vs files though.
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