The high school (grades 9-12) where I teach switched to the new UI in August. The thought was that we'd make the change prior to the semester start. We were able to lead our technology sessions for staff in the new UI, and that helped significantly. We also thought that since the resources in the Community were going to reflect the new UI, it would be best that our interface matched the resources available online.
I think your idea of changing during a break (holiday or semester) would make sense. However, make sure that you announce that changes will happen. That way, you can do some troubleshooting/Q&A before the new UI appears for users. We have a group of "Canvas Leaders" in our building, and we encouraged this group to investigate the new UI in our beta space before we turned on the UI for all of our users. That way, we had a support team in place for all of the inquiries at the beginning of the term.
Much like Brian, I have heard very little against the new UI - from teachers or students. At the beginning, the biggest adjustment our Canvas Leaders heard about was the location of the menus. Otherwise, the questions we had were on par with those we received with the old UI. With any technology, things evolve!
We haven't thought twice about our early opt-in with the new UI, and I believe that we would make the same decision about our timeline if we had the opportunity for a 'do over'.
@asatkins , if you would like to talk more about our rollout of the new UI, let me know! I'd be happy to collaborate.
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