Thanks for making me feel old. I remember reading slashdot a lot and also freshmeat.net to find new interesting software. I don't think I like the modern software experience, by comparison. It's all shoddy rehashing of the client/server model, where the client is crap and slow, and so is the server.
IIRC with Windows 98 you could just use any product key you had on as many machines as you wanted since there was no activation or real phoning home capabilities. So most likely your whole friend group would be using the same serial that was copied off your uncle's old gateway.
"If you play the Win98 CD backwards, it summons Satan. It's worse when you play it forwards - it installs Windows"
Ah, good times... :-)