It is the sort of mentality required to reach the place in computing which linux has. Decent chance you have linux running on something you own even if you do not run it on your computer and even if you don't, you do use the internet.

If your goal is to learn how it works this was great, a new challenge every day.

Perhaps we need a chaosmonkey Linux distro.

Also FreeBSD did this well recently, migrating libc and libsys in the wrong order so you have no kernel API. That was fun.

If you choose not to upgrade, it is stable. There is no QA department for Linux (or windows, they were let go around 2015) so someone has to endure the instability if there is to be any progress. We should all thank those who run nascent software so those who run stable distros can have stability.

You don't become a mechanic without fixing broken down cars. So in that sense, the shittier the car, the better.

My Linux story is similar. In retrospect I learned it on hard mode, because Gentoo was the first distro I used (as in really used). And Gentoo, especially back around 2004 or so, really gave you fully automatic, armour-piercing, double-barreled footguns.