I’m confused. Linus has repeatedly stated that the ABI should be stable, “we don't break user space”. There are exceptions, but any proposal that makes a breaking change to the kernel’s external symbols is very hard to push through.
I don’t remember anything breaking because of a new kernel version except device drivers, which are part of the kernel anyway and should be compiled for a specific kernel version. They are not applications, so they shouldn’t rely on assumptions about the ABI.
Most Linux distros offer mechanisms to compile a version-dependent interface to isolate a version-independent driver or program that messes too closely with the kernel.
> Some extinct “grown-up” OS like VMS?
I’d say the age of binary compatibility ended with most of those “grown-up” OSs becoming legacy. I usually test (compile and test) my C code on multiple platforms, ranging from Windows to Solaris on SPARC (emulated these days, sadly). I haven’t yet figured out a cost-effective way to test it under IBM z/OS’s USS (which makes z/OS a certified UNIX).