Booting could be an adventure. It helped tremendously to know that the LILO printed to the console at boot was itself a diagnostic, with the first 'L' indicating that the first-stage loader had been invoked from the MBR, and the 'I' that the second-stage loader was successfully invoked. Further error codes and behaviours generally indicated specific problems.

I'm having trouble finding diagnostic docs (understandably as LILO was deprecated over a decade ago), but the lilo(8) manpage has some details:

https://linux.die.net/man/8/lilo

As for installing Linux in 1998: I'd first installed Red Hat out of a CDROM from a book, and trialed Debian for the first time using a downloaded Potato (2.2) boot image -- the last installer that fit on a single floppy as I recall.

Instructions for a chroot install based on that were published soon afterwards.