I've just realized that until 100 reputation you don't get the upload image option in chat:
So that just means that the Upload Image button isn't there until you have 100 rep.
What would happen if one uploaded through the ask question's area and just copy pasted the link (very easy process)?
- Would the Image load since it's an imgur link (are they supposed to have the privelage, or is just supposed to be more inconvenient for them?)
- Would it just show the link
This is all you'd need to do: (then paste in chat box and it should load image)
I have not been able to test any of this out as I'm not a <100 rep user, but I'm very sure that it would work.