[SavantIdiot]

Macports made my life hard three times I upgraded OSes from having to migrate Macports versions, just leaving broken files in /usr/local/*. The worst instance was Mavericks, when it suddenly said i had no ports, after 10 years on the same image. It did something similar during the Monterey update. I'm now 100% brew but still have broken artefacts from MacPorts littering my system. I'm also still using the same image from 2012, moved to new machines with TimeMachine, so that could be it, but I'm damned stubborn.

[Isthatablackgsd]

Perhaps it would be great opportunity for you to clean install macOS to start anew and start fresh from there without worrying about lingering old files in the system.

[SavantIdiot]

I know, I know.

I tried to do a clean install on my 2012 MBP to get a feel for what would break. Unfortunately the 2012 is out of service and Big Sur kept powering down randomly. It runs Ubuntu 20.04 just fine tho.

I think OSes shouldn't atrophy. So I'm super-testing TimeMachine.

[pxc]

Homebrew packages break on major macOS upgrades, too. It's not up to the package managers what Apple does or doesn't rip out on a given release