One of the best choices our institution (a CCC) made when we began our own migration was to encourage our faculty to take the opportunity to move away from the use of files (pdf, docx, etc.) within the LMS, and to adopt the use of Pages (Content Pages) in Canvas. Our previous LMS had a the same type of feature, but had an inferior text editor, so PDF files became the norm. The bi-annual struggle to edit (update) such content was a challenge for our faculty, who never seemed to know where they saved the original MS Office file.
Aside from the obvious benefits of them reviewing/updating content, we emphasized other benefits such as using the Content Selector to link to other areas of the course, checking for 508 compliance, embedding multimedia (newly improved!), on-the-fly editing, responsive design, and of course the ease of access via the Canvas mobile app. Throw in the new duplication feature for Pages and it's a hard sell to use Files for anything other than primary documents, forms intended for printing, etc. Students are forever asking us where the file is saved to on their phone, or complaining about having to pinch, zoom, and scroll through a long file. A mobile friendly mind-set helps everyone.
I can report that this was well-taken by our faculty, and some have gone even further in this concept by using SoftChalk.