It would be very useful to have the system incorporate a built-in notification if the same image or document filename is attempted to be uploaded that already exists in the project. Then the user should have the option of overwriting (with all current usage auto-updating in the site) or renaming the new upload to create a new file.
Thank you @Kirk_Matkin for this suggestion.
I have created a feature request ticket for it.
For everyone who wants to support this feature, please comment here with a +1 and let us know if you also have some ideas regarding this topic.