I remember dealing with migrating from LILO to GRUB when I was in high school, maybe 2005ish? It’s been a while. I remember the migration from ipchains to iptables, too (which is happening again now with the iptables to nftables migration)
I used Ubuntu at the time… It was a great distro back then. I only had dial-up so couldn’t download large files easily, and Canonical or one of their local partners would mail you a CD for free regardless of where you lived in the world. I think that helped a LOT of people get into Linux.