What was your first videogame that made you say "Ok, I need to play this game properly: I need to upgrade my specs"?
Going back to your beginnings in PC gaming: the first game you played and loved, but the frame rate and resolution weren't ideal. Your first "I need/want to upgrade my specs" basically.
I had to run a boot disk because we couldn't run Windows 3.1 and Doom 2 at the same time. Good times.
My brother had a friend who knew how to upgrade computers, but we never got permission to do so. And then some years later my brother's friend was taken by the state because his parents believed some of that early Sovereign Citizen bullshit and stopped paying taxes. I think there were also some drug charges. It was just personal amounts of pot, but it was the early 90s, so they were fucked.