"The nerds hated microsoft for making them pay for an operating system."

The nerds hated microsoft because microsoft was (and still is in many ways) mandatory.

And they remained that by vendor deals, government contracts etc.

So everybody learned in schools on windows computers and with microsoft office and so on and so on.

Thats the reason, not because of money - it was allways easy to crack windows (I believe intentionally, rather a cracked Windows, contributing to the monopoly, than something else)