I rarely comment here on hackernews. I've also seen several flame wars over pipenv. I also believe that python packaging and pinning is nothing but a mess. Recently I started using Pipenv and suddenly I've been having horrific issues with python to the point of me almost giving up on the language itself. I believe the issue is a mix of Pipenv, Pip and Debian. I don't have full scope view of the issue yet but without evidence I believe the issue is how Debian uses Pip at the system level, and in pip 9+ an API used by Debian changed. Pipenv seems to greedly somehow upgrade my pip and thusly hoses everything and I find myself reinstalling everything. All three are making me consider making changes to my entire stack and setup that I've been using daily for the past 5 years on many many systems.
In addition when/if I have time I'll further debug and attempt at PRs and issues to help.