My team and I were discussing whether "Fill Area" was a better choice for our customers' Image Uploads or not. With it turned off, a customer may not use the full space, but with it turned on, they may lose some parts of their image they don't want cropped, and there's no way to see what's missing.
Another program I use for customization, ROES, defaults to Fill Area, but if the customer tries to move the image, it shows the ghost of what they will lose outside of the bounds until they deselect the image. I think this would be a great feature for Customily, and would reduce confusion and mistakes on what the finished product will look like.