I started using Linux right in the late 90’s. The small things I recall that might be amusing.

1. The installation process was easier than installing Arch (before Arch got an installer)
2. I don’t recall doing any regular updates after things were working except for when a new major release came out.
3. You needed to buy a modem to get online since none of the “winmodems” ever worked.
4. Dependency hell was real. When you were trying to install an RPM from Fresh Meat and then it would fail with all the missing libraries.
5. GNOME and KDE felt sincerely bloated. They seemed to always run painfully slow on modern computers. Moving a lot of people to Window Managers.
6. it was hard to have a good web browser. Before Firefox came out you struggled along with Netscape. I recall having to use a statically compiled ancient (even for the time) version of Netscape as that was the only thing available at the time for OpenBSD.
7. Configuring XFree86 (pre-cursor to X.org) was excruciating. I think I still have an old book that cautioned if you configured your refresh rates and monitor settings incorrectly your monitor could catch on fire.
8. As a follow on to the last statement. I once went about 6 months without any sort of GUI because I couldn’t get X working correctly.
9. Before PulseAudio you’d have to go into every application that used sound and pick from a giant drop down list of your current sound card drivers (ALSA and OSS) combined with whatever mixer you were using. You’d hope the combo you were using was supported.
10. Everyone cheered when you no longer had to fight to get flash working to get a decent web browsing experience.