In my experience this is less to do with the fast pace of development, and more to do with the fact that many engineers use virtualenvs, and virtualenvs "vendor

In my experience this is less to do with the fast pace of development, and more to do with the fact that many engineers use virtualenvs, and virtualenvs "vendor" the pip version so you need to update pip in each virtualenv you use. This is correct, but does lead to needing to upgrade so much.