I have/had 10 guitars, from both eras, with this bridge pass through my hands, and I've installed these strings on all but 1. Never had any issues.
So, I happened to travel the next day to the nearest town with a big-box guitar store, and bought D'Addario EXL110 nickel strings (same gauge). This brand installed without any resistance.
I looked closely at the bridge on this guitar, and the holes are sunken below the level of the inside portion (where the saddles reside). I'd estimate that about 20 to 25 percent of the hole is blocked. Imagine if you were onboard a passenger ship, looking out a row of portholes, and they were partly below the water line. I tried to take a photo:
The overall thicknesses of the .046 D'Addario wrap end and the Pyramid wrap end are nearly the same, to my naked eye. (I don't have a micrometer.) Nonetheless, the Pyramid clearly has the widest section at the end of the wrap. The Pyramid wrap does extend farther up the wind, but that doesn't matter. On my other guitars, that section passes through the hole and toward the saddle, and the ball fits snugly against the interior as it should. Here's a comparison photo, with D'Addario wrap end (left) and the Pyramid end (right):
Has anyone had similar issues? Any thoughts, ideas?