[worik]

I think you are exaggerating.

Computers of all stripes are more reliable now. In the late nineties I ran apache + mod-perl built from source.

We had a lot of problems, but I cannot recall ever having a problem with those two.

We tested every update, of course, but it was not a huge burden.

[surge]

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.