Updating this site
Major updates (the ones where the second or first number in the Word Press version changes) often introduce new features and functionalities that have not yet been shared with a larger audience.
Changes to these files will be overwritten upon update, making your customizations obsolete. By default, every site running Word Press has automatic updates enabled for minor core releases and translation files.
While convenient, the automation of this process is not always helpful.
Plugin developers are often slower in bringing their creations up to speed when the next Word Press version hits.
Keeping your site updated with the newest version will give you the latest and greatest that Word Press has to offer. Unforeseen hiccups, compatibility issues with plugins, and other unfortunate consequences are not unheard of.
More than a few users have had their site break, experienced downtime, or lost data due to problems with the update process.
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Of course, that is something all of us want to avoid.