I guess I missed the part where you explained how it makes sense to
    apply a label like "not recommended because it supports non-free
    software" to OpenBSD but not to FSF (emacs, etc.).

As I've said, I think it's acceptable for free applications to run on
non-free platforms (and say that they do), because this doesn't
recommend the installation of those non-free platforms.  But free
systems should not recommend, suggest, or offer to install non-free
apps.

I follow these principles without discriminating between people
or groups.

Thus, I think it is legitimate for apps to run on Windows, so I apply
this to both GNU applications and OpenBSD-related applications such as
OpenSSH.  I recognize that this can have the negative effect of
reducing the pressure for people to move away from Windows, but I don't
think that alone is a reason to reject apps that can run on Windows.

Meanwhile, for operating systems, I endorse the ones that don't
recommend, suggest, or offer to install non-free apps.  I apply this
principle to GNU/Linux distros and to BSD distros just the same.

When people discover a recommendation for non-free software in a
distro which is supposed not to have any, my first response is to show
it to the distro developers and ask them to remove it.  Everyone makes
mistakes, so my aim is to get the mistakes corrected, not jump down
their throats.