I've uploaded 10 or 12 images in between 2010 and 2013 and I've never had a problem. It's actually been quite simple for me. My first few uploads were actually before there was any official system set in stone, one even before the tsunami of personal emails to classic staff (if anyone remembers that). But I can understand your frustration based on your explanation.

It sounds more like an issue with how certain staff handle the task, and would probably be best suited talking to the chief in command of the staff division about your experiences and suggestions. Perhaps something can be done to make sure every uploader is on the same page, and the system will consequentially become more consistent. Worth a shot!