I’ve actually tried to do that with pictures/art, but none of the tools I have to do so make it easy. The Windows photo viewer from Windows XP, which I can’t seem to get anymore, was actually pretty okay at it.

But the truth is that even then it required more effort than I was willing to put in, and I was never able to anticipate every tag I would eventually want. If I didn’t feel like tagging something the moment I saved it, it generally never got tagged.

At this point an AI to do it would be amazing. I have thousands and thousands of pieces of potential character art, but when I want something with specific features it’s not easy to find.