When I was actively using SageMathCell for teaching, I indeed got quite irritated that things that used to work during preparation did not work in class because of some recent changes. My eventual solution was to run my own server, where no changes were ever unexpected and in general I had better stability. I think this is still the way to go for those who want to be certain that things will work, although I have a feeling that not very many people are doing it. Python version change is likely to be the most disruptive one, so it may make sense to do it only during the summer or around New Year, so that we don't cause major disruptions in the middle of the course. Perhaps UTMOST people may chime in with their predictions on how bad the transition would be?
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