I got a free License of windows 2.0 and an old dos version, cant remember what version it was tho, same went on when I bought a 386 16MHz. So I had legit versions untill windows 95, I got my first version of windows 95 from a BBS, it was the floppy version. I got my hands on a W98 license allmost for free.
Then I did stick with w98 untill Windows XP came, then I did use a pirate version because then I did not use Windows much, I mainly used Linux and dident use Windows enough to justify the license cost.
I skipped Vista but now have a computer dualbooted with W7 pirated without any troubles to use Windows update and no fails at WGA checks. But I do not use Windows much, I tend to keep using Linux since its what im most famillar with on x86/x64 architecture.