[Jim A]

Nice vid!
It almost seems like the first try bumps into a tooth but aligns the mesh just enough for the second try to fit.
Sometimes the first alignment is OK.
Maybe it doesn't hit a tooth, but doesn't move far enough to make the internal electrical contact which would boost the gear into meshing.
I can't remember what changes you made that preceded this unfortunate situation, but I admire your tenacity and am sure clear skies are just ahead.

I am not sure how much I should risk jinxing my Jimmy and me, but I don't remember replacing or rebuilding my starter in 52 years.