> Python 2 to 3 is a good example of what can be expected to happen

People keep bringing this up when discussing backwards compatibility breaks, but I think the conclusion should be a bit more nuanced than just "backwards compatibility break <=> years (decades?) of pain".

IMHO, the problem was the backwards compatibility break coupled with the inability to use Python 2 code from 3 and vice versa. This meant that not only did you need to migrate your own code, but you also needed everything you depend on to also support Python 3. This applied in reverse as well - if you as a library developer naively upgraded to Python 3, that left your Python 2 consumers behind.

Obviously the migration story got better over time with improvements to 2to3, six, etc., that allowed a single codebase to work under both Python 2 and 3, but I think the big takeaway here is that backwards compatibility breaks can be made much more friendly as long as upgrades can be performed independently of each other.