Some thoughts on Ubuntu upgrades.
https://popey.com/blog/2021/01/upgrading-ubuntu/
“So I feel it incumbent on those of us who are technically skilled to un-break their system if it does go wrong, to do these upgrades and find the sharp edges so our “normal” users don’t have to.”
Yes! Just this weekend my dad ran into an ecryptfs problem on upgrade. After ~15 minutes' debugging he gave up and reinstalled. Before he upgraded, he expected it wouldn't work and he'd have to reinstall, which is why he was happy to give up so quickly. Sad that he had that expectation.
@popey Of course I'm biased because Endless OS works like this , but I think snapshot-based OS updates with rollback are part of a solution. But still it's hard to make rolling back seamless, particularly downgrading system config.
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@popey He is not quite skilled enough to diagnose the problem himself, and I'm too far away to help him do it remotely. Frustrating. He can't be the only one hitting whatever it is.