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Upgrade Arch, on a whim.
(thelemmy.club)
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I had one Raspberry Pi that needed to be hooked up to a monitor after it failed to reboot after an Arch kernel upgrade. The device name for the Ethernet card changed, and the netctl setup I was using to set up some route or other no longer worked.
In my years of using Arch that was literally the only problem.
I've had pain with several Debian upgrades, mostly due to exim4 becoming more strict and me actually having to learn something about my email setup. Also an issue with a Debian upgrade changing Dovecot version. Neither really avoidable by Debian, but it was not less painful somehow than Arch.
Actually this reminds me of why I moved to Arch on Raspberry Pi. I had a SD card go bad, and ext4 just happily used corrupted data. I wanted to switch to btrfs, which I could do with Debian, but any time Debian updated the kernel it wiped my setup and I had to do work to get it booting again. Arch supports btrfs out of the box and has worked smoothly and easily.