I develop in python since 10+ years. And setting up a virtualenv only happens when developing patches for 3rd party packages. (due to the other commercial environment that doesn't work with venvs).
And it is a totally miserable experience on Windows, every single time.
If only that were the norm amongst long-tail python users. Heck I don't do it; I have the anaconda distribution installed on Windows and when I need to do a bit of data analysis hope I have the correct version of packages installed.
Making this core to the python workflow (bundling virtualenv? updating all docs to say "Set up a virtualenv first"?) is the first required change, before thinking about unbundling stdlib