What about people who dip their toes in Python, then switch to another language? What about people who want to just replace their VBScript integrations with Excel and don't care about Python beyond 1-2 dependencies on local? You'd just push them back towards the less optimum situation.
Oh, and I just remembered, Windows 10 Home Edition does not ship with a hypervisor. You can't run Docker on Windows without Windows 10 Professional. That screwed my team over at a data science hackathon once.
If you're at the point where you're worrying about distribution environments, you're probably ahead of most people already, and you have the wherewithal to figure out what the state-of-the-art is in packaging and distribution, whatever that may be and regardless of how broken it is.
However, the software distribution model right now is fundamentally broken. And I do not think it is worth leaving broken simply because it makes learning easier for some people.
In general, I think the decision to push people to tie their app less to the system configuration and rely on virtualenv, containers etc more is a good move in the long run.