I think the question goes back to the size and scale of users at the 1 to 2 jump versus the 2 to 3 jump. Python didn't really start to hit most of its "forward progress" in terms of both user adoption and being so deeply integrated into systems. There was no Django for Python 1, for one example. As another example, I'm pretty sure Debian and its heavy reliance on Python for so much of its system scripting didn't happen until Python 2, either, but a quick search didn't turn up a reliable date.
It probably would have been a lot less risky with so many fewer daily users, so many fewer huge projects to migrate.
You may be right. I first used Python on a regular basis in 2002 (after release of Python 2), so I wasn't aware it had so little adoption prior to Python 2. But it definitely was picking up by 2002.
It probably would have been a lot less risky with so many fewer daily users, so many fewer huge projects to migrate.