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dev/sg: improve error handling in updates

Administrator requested to merge sg-update-improved-errors into main

Created by: bobheadxi

Some users reported sg installations getting botched (https://sourcegraph.slack.com/archives/C01N83PS4TU/p1657925934690789) - this might have been fixed by #38848 , but just to be safe I did an audit of our error handling in auto updates and found a few places to make some improvements.

Test plan

n/a

Merge request reports

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