Debian is the one distro I constantly break, I feel like APT is a flimsy package manager as it can totally death spiral into breaking your whole configuration, so it's actually crazy impressive that you keep them running, kudos.
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I'm primarily a FreeBSD user but have Debian for things that vendors only release .deb binaries for so maybe I've just been lucky, but the only serious issues I've had with apt is when I install things without regard for mixing versions, thinking "what can possibly go wrong" and then shit goes wrong
Part of admining Debian is learning to fix it, but apt problems are *extremely* rare on stable. However upgrading oldstable->stable or on unstable, it does happen. Caveat: there's always enough rope to short yourself in the foot, definitely can break things (unknowingly) doing something stupid.
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