A month ago I had to fix a small bug in Python 2.6 code in one of internal systems. It won't be ever migrated, no capacity and no value

It was annoying but if it hadn't happened Python would still be struggling with basic things like Unicode.

Organizations struggled with it but they struggle with basically every breaking change. I was on the tooling team that helped an organization handle the transition of about 5 million lines of data science code from python 2.7 to 3.2. We also had to handle other breaking changes like airflow upgrades, spark 2->3, intel->amd->graviton.

At that scale all those changes are a big deal. Heck even the pickle protocol change in Python 3.8 was a big deal for us. I wouldn't characterize the python 2->3 transition as a significantly bigger deal than some of the others. In many ways it was easier because so much hay was made about it there was a lot of knowledge and tooling.

It was not a disaster in any way. People just complained about having to do something to upgrade their codebases.

Except that Python took the other path when migrating from Python 1 to Python 2 and ... guess what? That was a "disaster" too.

The only difference was that by the time of Python 3, Python programs were orders of magnitude bigger so the pain was that much worse.