For paper artworks of significant value, rolling would be considered damage, which would reduce value. For that reason, even moderately-priced limited edition prints are generally shipped flat.
For paper images that are replaceable or have no long-term value, I roll with the image to the inside. This way, when the paper is unrolled and the edges are held down by the mat or glass spacer, it lies flat when framed. If the paper were rolled the other way, with the image to the outside, then it would tend to bubble in the center when framed.
Canvas should always be rolled with the image to the outside, so that the paint layer is stretched instead of compressed. Thye paint layer may crack, but when unrolled, the cracks in the paint layer would tend to close themselves and would not be visible. If rolled the other way, with the image to the inside, then the paint layer would show visible cracks when unrolled.