The Python 2 to 3 transition took a while, but I'd say it was successful in the end, wasn't it?
For example:
- I think they bungled the Unicode transition by being too dogmatic and it took them a few point releases to include some quality of life improvements for migration that really allowed legacy libraries to transition
- the GIL dependency didn't go away
- typing was added later
Python 3 would have been a huge jump with those changes. Instead, Python 3.0 was very interesting but a major annoyance for limited benefits to 99% of Python app devs.
There's some serious work going on with the GIL these days. And also about immutability and reducing reference counting.
> [...] it took them a few point releases to include some quality of life improvements for migration that really allowed legacy libraries to transition
I wouldn't hold that against the transition too much. No one gets everything right from the start.
About typing: owing to Python's culture, I don't think mainstream Python will be statically typed by default (or even obligatorily) anytime soon.