“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.