No kidding. I pretty much don't even believe in the concept of a serious upgrade anymore, as far as pip goes anyway. As long as it still works when I run it, nobody is missing out on any serious upgrades as far as I'm concerned at this point.

Fully agree with this. That line has become "invisible" to my brain.

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.