[tzot]

At work we had a very-late-technical-debt-move from “Python 2.7/Django 1.7” to “Python 3.8/Django 3.2” (with lots of associated libraries moving forward too) and we managed to reach a point where our codebase was common and functioning in either environment; the process was… bloody, to say the least, and obviously I wouldn't wish for others to ever have to go through a similar ordeal, but it was feasible.

In any case, I don't think that in the Python ecosystem there will ever be another jump of the same magnitude as 2 to 3.