Earlier quoted context omitted.
I think the biggest problem is going from zero third-party dependencies to one and more. Adding that very first one is a huge pain since there are many ways of doing it with many different trade offs. It is also time consuming and tedious. The various tools like you mention are best at adding even more dependencies, but are hurdles for the very first one.
Not true. The more external dependencies you add, the more likely it is that one of them will break. I try to have as few external dependencies as possible, and to pick dependencies that are robust and reliably maintained. There is so much Python code on GitHub that is just broken out of the box. When people try your software and it fails to install because your nth dependency is broken or won't build on their system…
[1] https://github.com/jazzband/pip-tools [2] https://docs.pipenv.org/en/latest/ [3] https://tox.readthedocs.io/en/latest/