Sometimes I run into a plugin that really blows my mind with how useful it is — especially when it's also free. The Enable Media Replace plugin is active on over 100,000 websites and has been on the plugin repo for six years. So, maybe I'm just that late to the party. Maybe you are too.
Enable Media Replace allows you to replace attachment files by uploading the new file on the attachment edit screen. It then replaces that file throughout the site, wherever it is used. It's super helpful.
Hat tip to WP Shout for the find. Maybe you'll find some other things you didn't already know in their post on five “WordPress wins”.