I think you're romanticizing it. Until RHEL and LTS releases for Debian/Ubuntu, most distros you never knew if running and update was going to break something because there simply wasn't effective quality control testing in the hobbyist distros. Best you could do was run a version behind, but that hurt if you needed security updates.
There were plenty of people and small highly knowledgeable shops and academics that thought 6 hours fixing a bug after custom compiling a patch was fine and normal (and a RHEL subscription at least meant RedHat would have a team doing that part for you if absolutely necessary), but its not the way companies operated. RHEL at least meant whatever release was stable and an actual QA team put patches through their paces on various hardware and configurations (especially those enterprise high end server configs with special SCSI/RAID controllers, high end network cards, and other chipset other distros simply didn't have the means to test on). The QA/support team wasn't bug reports and guys on usenet going "it works for me, you should have gotten the exact same hardware I have, or be willing to go through the code and figure it out and patch it, and submit it to the source, like a good user should". Or tell you go back to Micro$oft if you want support for your storage controller that the kernel module for worked fine in the last version. Those were the zealots, the rest were sys admins with too much other things on their hands to do than deal with Slackware or whatever the hot distro was on distrowatch.
My Redhat experience always seemed to devolve into "this package that I want has a dependency that isn't listed yet..." (cue 2 hours of recursively and manually tracking down dependencies on the early web).
But I was a lot younger and didn't know a lot of what I do now, so was probably doing everything RPM wrong.
I had the dependency spiral issue on every distro (I played with quite a few), compiling with something like Gentoo made it worse. RPM Forge existed, I think the Linux experience in general was bad back then, and RedHat actually was one of the least problematic. Until Ubuntu, it was the easiest and most approachable to use for novices.
Using redhat before yum, meant visiting rpmfind.net and manually collecting what you needed.
In some ways, RHEL is still like that, because popular packages are usually a major version or two behind if they're even there at all. You have to hunt down an EPEL that has whatever you need.
Yeah, I don't miss the old days. Like another poster though, I remember apt-get being decent while pre-yum RedHat was still pretty bad.
But I also realize my perspective was that of a hobbyist, not an enterprise sysadmin who was probably upgrading to well-known versions through known paths.
I worked with sysadmins who used rpm based distros back then and their experience was basically mine: hunting down the right rpms that both satisfied the constraints and actually worked.
If you were running Apache fine, I think Linux in the late 90s was the work horse of web servers. That might have been the one thing that just worked. I was using it as a workstation and for everything else. Try getting your window manager to work with your Xserver and graphics card. Upgrade a package that needs a newer packlage, that needs another package that no one has built yet, so now you need to custom compile the library, but if it replaces the existing library it breaks something else that relies on the older library.
That's inbetween figuring out how to get things to compile and the dependencies of dependencies, etc.
I got Linux to work, but it was also a love hate relationship, when I got it working, it worked and worked for months, but I had almost a PTSD reaction when it was time to upgrade anything, I knew what was coming and I was afraid.
