Perhaps scenarios like this are what are annoying people...
In the early 2000's, somebody creates an article about the notable actress [[Francene Foo]]
Somebody finds a publicity photo, ffoo.jpg, uploads it and links it.
It gets deleted because the uploader forgets to give it a license.
It's re-uploaded and properly tagged as fair use.
It gets tagged for deletion because someone feels it can be replaced with a free image. It survives.
On another part of enwp, it's decided that fair use images should have rationales. It's tagged again.
A rationale is added.
The rationale is disputed because someone else feels that someone somewhere must have a free image. It survives again.
Another group of Vogons decide that fair use rationales should include the name of the article they're used in. Some bot comes along and flags it.
The rationale is updated one day before deletion.
After a discussion on [[talk:Francene_Foo]], it's decided that the article should be moved to [[Franny_Foo]] since she is better known by that nickname.
The bot comes back and tags the article again.
The rationale is once again updated to reflect the article's new name.
Franny Foo then marries Billy Bar and starts to use the name "Franny Foo Bar" professionally. The article is then moved again.
Here comes that frackin bot again. Lather rinse repeat.
Someone then decided to use ffoo.jpg in [Angels with Pogo Sticks] which is a movie Franny starred in. Once again the bot tags the image.
This is kind of an extreme scenario but I can now see why some are annoyed.