Packaging will refuse to progress if the history has errors (https://community.esri.com/t5/arcgis-pro-questions/packaging-error-00246-history-items-with-errors/m...). This idea is to (optionally) allow packaging even if there are errors. Often the errors are the very reason for sharing a package, to see if someone else can solve or reproduce the issue.
(Besides, I often encounter history packaging errors for items that are merely warnings, "output will be overwritten" for instance.)
(post edited based on responses to increase clarity)