That's a tricky question. Upgrades are intended to only fix things and not break them 😉
In each release note, however, there is a list of 'known issues'; this is the list of issues we are aware of that could pose a problem, so it's recommended to review these before proceeding.
There is also a list of changes to default behavior, if you're upgrading from one major version to the next, that would be of interest to make sure everythig keeps working as expected
Anything that is not listed is either being investigated, being fixed or not known to us yet, but if we do find a glaring issue that would affect many customers we do send out notifications through all channels (emails, community posting on the Live main page,...)
hope this helps
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