Dear Alex: my bum vision kept me from appreciating some of the features of that lash-up. And the artist failed to have some proportions optimum. If started with ropes hitched by those snap-hooks in optimum position, the barrel could be rolled pi times diameter, which could equat the height of the plank that is the ramp. If slippage were not a problem, the barrel could climb far enough to tilt the plank to lie horizontally. The axis of the barrel would rise only about equal to diameter, so the mechanical advantage would be about pi, or three times, better than I thought at first.
So for such a short lift, the apparatus would work. But the ramp length could not be greater than pi times d.
Thanks for the fun of thinking about it.