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I haven't found updating PropertySources all that risky in general. From my understanding PropertySources can't remove any existing properties so even if it stops adding some that are needed after upgrading it, it would only affect new devices. In general, we check new devices are working as expected so if that did occur we would likely catch if that happens. But I haven't done too many PropertySource upgrades recently. Generally other checks mostly just look at system.categories rather then auto properties also.
Now Sysoid, that I worry more about since you can't really check what will happen before updating it :)
PropertySources can remove properties they set. If a new version of a propertysource runs successfully and doesn't output the same properties as before, the properties from before get replaced with the existing ones. The only exception to this is system categories. If a propertysource sets a system category, it won't remove it, no matter what.
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