I agree that there needs to be a new system, but there are logical reasons as to why these things happen. The image you want uploaded is important to you, it is not important to most admins. They see a lot of heads/shields/bodies/etc come in each day. If it doesn't meet the servers criteria then they will be quick to discard it and probably won't go into too much depth to explain why.
Why is that? During my experience as an admin, I would try to explain things in detail to various people. Whether it was in-game or via e-mail. The conclusion was usually the same, it was some 12-13 year old with broken English who couldn't understand why their image wasn't added or why they were running into a certain problem. No matter how much you tried to explain they just wouldn't get it. That takes a lot of energy, especially when doing this with so many people and then the problem is usually never resolved.
I can't speak for admins, but I am guessing they really don't care if you image gets uploaded or not. Because its not worth the effort for just one head to get uploaded. Just my opinion.