Here's an update that sure makes the bad cavity idea make sense. I cleaned the die and went ahead and sized a few more and most were sized evenly around the entire boolit. The grooves are still being squeezed smooth but it's pretty much even.

I made up a dummy round and got it to plunk at 1.020 in the Lone Wolf barrel out of my Glock 17. I have 1 other Glock with a Lone Wolf and 2 others with stock barrels.