I'm glad you mentioned SSL. Because hey - that broke some scripts in 2.7.9 ;-)
https://www.python.org/dev/peps/pep-0466/
(Can't remember the details, but it may have been something about some extra hoop you'd have to jump through to trust self signed certs that broke our testing infrastructure)
Totally agree - I just don’t see that as a distinguishing factor since we had a bunch of shell scripts break, too, as various CLI tools stopped behaving consistently.
I guess this is a YMMV thing. My experience is that Python rots more than shell scripts, but of course I understand that this may not be universally true, and depends a lot on what your scripts actually do (and, to a large extent, on how they're written, of course).
Over the years I've spent way more time going into inconsistencies about the various platform tools (e.g. GNU vs. BSD implementations of sed, grep, find, etc. even before you ge to the space aliens-with-broken-translators realm of AIX) — which using Python avoided needing to care about — or library / file naming changes. Similarly, a few years back there was way more time used when various HTTPS improvements flushed out code using old versions of OpenSSL or, worse, gnutls.