The bent radius thing is a data given by the rope manufacturers, either steel or textile rope. It doesn't say that you will drop your load with a tight radius, but that the load allowed on a rope decreases as the radius is smaller. So the WLL is reduced by a certain amount. The recommended radius is the value with an acceptable reduction. Going farer than that is possible but at the cost of a substantial loss of both rigging capacity and durability. You could very well never see the difference, because it's hidden in the safety margin, at least if you don't push the thing too far. But your safety margin is no longer 7 as it should be but more like 5 or less. That lives less room for the other hazards affecting the rope.
I may be looking at it wrong
I'm afraid you do.
It isn't a matter of load, length, size, or even angle, but just curvature.
Just look at it closely, not the wide view of all the device, but follow bit by bit the path of the rope.
On a pulley, the rope first comes straight, then bends and takes the shape of the pulley, rides all over the pulley with the same bend (constant radius of the groove), then lives the pulley and straightens back.
On the three stacked rings, the rope first comes straight, then bends and takes the shape of the first ring (way smaller radius than the pulley). After a bit of riding on the ring, the rope lives it and straightens for one inch or so, then the rope finds the second ring, bends again on it to take its shape and slides to the other side.
Here, the rope lives the second ring and straightens for the second time, taking a small travel in the air. The rope finds the third ring, bends again to take its shape as previously, slides on it for a bit, finally lives it and straightens for the third time.
You can see that the rope only took the shape of the rings individually and was never close to the shape of the first case with the pulley, even if the overall size of the stack can match the size of the pulley.
Now, for the flattened pulley, the rope actually sees two tight bend radius on the edges of the flat spot.