I read the above sentences as: 1) the legacy on $SYSTEMS_I_DONT_LIKE is bad 2) the legacy on $SYSTEM_I_LIKE is there for a reason.
I can still run software written for Windows 95, without recompilation, with a pretty high success rate. As far as I'm aware, only Linux has that level of ABI compatibility and unfortunately it's completely broken by userspace. Often you can't even run the same binary on two different distributions without recompilation.
True, though 32-bit editions of Windows still include NTVDM which runs Win16 apps!
Microsoft is pretty fanatical about backward compatibility.
Why? It's the #1 reason most enterprises and many users continue to pay to install/upgrade to Windows.
Breaking backward compatibility with existing executables (not source-code) is a violation of the trust that we've earned with customers for the last 40 years or so.
Of course, some products/features/etc. are discontinued on newer OS', etc. but the core essential platforms are rarely discontinued.
True fact: Windows still runs VB6 apps - millions of them. EVERY DAY!