That would seem to be ironic. As a longtime Perl developer who switched (for pragmatic reasons -- a job) two and a half years ago, my impression is that Python [as a language] is much better suited to a business environment. What makes Perl such a wonderful language and why I enjoy it so much is exactly why it blows as a business language. Python's rigidity is very useful if you ever want someone else to read and understand code written by someone else. So the idea that Perl ends up with the more mature package management is exactly the opposite of what I would have predicted.

That said, I haven't had any more problems with PyPi packages than I did in the past with CPAN. Yes, pip always wants to upgrade itself, but that sort of every-damn-day software upgrade cycle seems to have become quite prevalent, not just in the Python world.