Wrench,
When I had my 418 stroker I needed a gear drive starter for it and I went to a local shop that built me one and when I put it on the teeth on the Bendix wouldn't engage the flywheel. I called them and they sent a tech to look at it. He got under the car and pulled the starter to see if I had anything lined up wrong and immediately told me he saw the problem and he would be back in about 30 minutes. He took the starter and I asked him what was wrong and they had put a front on it for an automatic transmission instead of the 5 speed and he said that front wasn't as long as i needed and he would put one on that would work. He came back in around 30 minutes and I could see the difference in the starters length. He put it back in the car and wired it up and it is still in there today. I am sure that this isn't anything to do with your problem but I had a thicker block plate than was standard. I wish we could still get service like that here today.
Ron