I agree completely Jim.  The problem is that OpenSSL regularly discovers face-meltingly bad security bugs, so it frequently pulls the "security exception" lever.

As with so many things in this life, we play the hand we're dealt.  I have my fingers crossed that LibreSSL will, in the long run, be far more sane, and that we can switch to it someday.  But for now I expect to have plenty more "necessary" OpenSSL upgrades foisted onto Python.