Did you notice this: "He has already put into motion the conversion of the Dropbox server code from Python 2 to Python 3." Even the company that hired Guido is still heavily dependent on Python 2, and it doesn't surprise me at all; my own employer still has a lot of it in internal tools.
Don't they have source to source compilers that do the migration for you? I don't understand why the friction is so strong with python.
Fundamentally the issue is that the Python language is too dynamic for static analyzers to fully understand the code and perform conversions. I'm not just talking about type systems, but also monkey patching, reflections, etc.
What we really need is a tool that runs your Python 2 code, records types and other dynamic manipulations, and then produce Python 3 code. But I'm not aware of such a tool.