Maybe I'm still misinterpreting, but this was where my mind went. Man, I wish I could've appreciated how distinct the 90s were as a kid, but I was too young and dumb to have a shred of hope of being that aware!
I never 'totally borked' a PC with LILO but definitely had to fix some things at least once, and that was with a nice thick Slackware 7.1 book to guide me.
GRUB, IIRC, vastly improved things but took a little while to get there and truly 'easy-peasy'