I have an interesting situation with my 19 hack.
It originally was a non-starter and I replaced the motor with a 25 because I wanted to protect the original one.
I couldn't get the crank to engage correctly so I installed the starter to get things working.
Now I am working on the crank.
The first thing I did was replace the bushing because it was very sloppy - it still didn't engage well.
Next I realized that I didn't push the new bushing in far enough, so I fixed that. Still didn't engage.
Next I replaced the ratchet because it was very worn. Didn't work.
This weekend I pulled the radiator so I could see what I was doing and found that the pin that held the pulley on was the short one and it needed the long one.
I had a long one and figured that it would finally fix the problem.
I put things back together (except the radiator) and it still didn't engage correctly.
Finally I noticed that the center of the shaft on the crankshaft did line up with center of the crank. The crank was about 1/2 inch high. This made the inside of the ratchet interfere with the OD of the sleeve on the pulley.
All that I figure is that the snout on the pan is bent
If what you say is true, I think you are in line for a pan straightening. This is done with a pan anvil but you will have to take the engine out and remove the pan. You could save a broken crank by doing this. If all the mains (including the forth at the drive shaft) are not in line you could be putting too much pressure on the crank. Just my .02.
I should have said that they do not line up
What kind of crankshaft belt pulley do you have? Some of the aftermarket aluminum pulleys have too much metal behind the pin and the ratchet won't go all the way into the pulley to engage the pin.