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While there is a snarky, "I'll show those big software companies" case for one copy/many installations of software (and that's harder all the time) one of the reasons South Korea got hacked so brutally about a dozen years ago was there were an awful lot of unregistered, older, copied, bogus installations of Windows that were easy to exploit.
This is a very "pick up nickels in front of the steamroller" thing. But the bad guys in cybersecurity are very, very good, and there are an awful lot of nation-states that will run rampant on those who are actively choosing to be the low hanging fruit. Which is what happens when you run old, dodgy software.
