Living through it... Python 3 made a lot of changes for the better but 3.0 in particular included a bunch of unforced errors that made it too hard for people to upgrade in one go.

It wasn't until much later (I would say 3.4 or 3.5?) that we had good tooling to allow for migrating from Python 2 to Python 3 gradually, which is what most tools needed to do.

The final thing that made Python upgrading easy was making a bunch of changes (along with stuff like six) so that you could write code that would run identically in Python 2 and Python 3. That lets you do refactors over time, little cleanups, and not have the huge "move to Python 3" commit.