Your example just goes to show the absurdity of comparing PyPI to Trisquel's
repo. What you're talking about is a third party, the author of "DOZ" in your
hypothetical example, giving instructions for installing a proprietary
program. Surely you've seen proprietary programs being distributed with
instructions before, without ever having a need to reference pip! I can
easily think of several examples off the top of my head, like Google Chrome
(which distributes a deb file as one option, and that's much easier to
install than something from PyPI; no need to install any new software).
All kinds of reductions to absurdity can result from your argument, but here
is the most troubling: if the fact that proprietary software developers can
make it super easy to install a proprietary program is a problem, and it's
possible for them to do this regardless of whether or not PyPI is there to
help them, does it not follow that Trisquel must become a jail which forbids
installation and execution of proprietary software?
I don't see any problem with PyPI as such. pip is not recommending
proprietary software; it's just offering the same convenient way to install
proprietary programs as with libre programs. It might be the case that PyPI
could put pressure on proprietary software developers by only allowing libre
software on it, but that's a matter of strategy, not ethics.