The one on the left is better than the one on the right to me. What cutter angle did you use? I get further onto the shoulder with a K&M +3* cutter, a wider but shallower cut area. My cutter makes a less abrupt transition than yours looks like, but that might just be the picture. Looks like a Weatherby so I'm not sure how the angle interacts with a radiused shoulder. K&M makes an inside reaming mandrel if I get into donut trouble, but looking at results I doubt I will using the correct cutting angle and a bushing die.
For me it's a one-and-done process on new brass. Some people disparage it, but I view it like uniforming flash holes - it doesn't hurt, it doesn't take that long, you only have to do it once. It's all voodoo anyways.