Your problem is the teeth of the starter drive are jamming against the ring gear teeth, both of which are probably getting worn. Replacing the starter drive will probably help, but if not you will need to either replace the ring gear on the flywheel or use a Dremel with a 90 degree adapter and a reinforced cut off wheel to reach in through the starter hole and reshape the edges of the ring gear teeth. I have done it using a small file, but that takes a lot of time. There will be 2 stretches of a few teeth each that are dubbed off due to the fact the engine almost always stops between compression strokes.
Loosening the starter bolts a round or so each will make it easier to break loose. Normally at that point you can turn the crnk to break it loose.
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Today's Featured Article - Memories of an IH Super A When I was ? up to 10, I worked on my Papaw's farm in Greeneville, TN every summer. As I grew older (7), it was the thrill of my day to ride or drive on the tractor. My Papaw had a 1954 IH Super A that he bought to replace a Cub. My Papaw raised "baccer" (tobacco) and corn with the Super A, but the fondest memory was of the sawmill. He owned a small sawmill for sawing "baccer" sticks. The Super A was the powerplant. When I was old enough (7 or 8), I would get up early and be dressed to
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