MS's attention to piracy -- to my remembrance -- became more intense after Windows 2000, or so I thought it did. I actually had an OEM 2000 disc which I was able to install on at least 2 PCs in the house around the turn of the millennium, without problems or repercussions.
So the activation phenomenon began with XP -- particularly with the knitting of a hardware hash code to the OS, or at least the OEM white-box OS.
On the matter of the Law, I saw my use of Win 2000 Workstation as falling into a gray area. The machines were all connected to the web via the same router connection; I didn't use them for business; I myself was mostly the only user; they were all installed within the same household. And I probably didn't follow the EULA restrictions. But that didn't last long.
When we struck up our broadband subscription around 2000/2001 with our cable provider, they sent a tech person to the house to set up the cable modem. During casual conversation, I asked him how I could get an inexpensive installation of 2000 Office Pro. He went to his truck and brought back a homemade install disc, which he gave me. But that didn't last long, either. I can't remember for sure whether it was a problem of upgrades or something else. But I soon became comfortable with paying for my software the way the manufacturer wanted me to pay for it.
The benefits outweighed all the possible costs you can think of.
I wouldn't touch pirated software with a ten-foot pole. And that's especially true with software from MS -- according to that very same calculation of costs and benefits.
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