"Meanwhile, openssl and bash, while getting security updates very recently, are in their very latest versions still compatible with programs from probably over

"Meanwhile, openssl and bash, while getting security updates very recently, are in their very latest versions still compatible with programs from probably over 8 years ago." You have obviously never worked with OpenSSL. Also, the problems with `pip` is entirely due to Ubuntu not updating their dependencies properly. Upstream `pip` vendors their dependencies so that this precise situation does not occur.