Sounds like the constant mesh gear on the counter shaft may have stripped the keyway. But I don't understand how it will start pulling again. Unless its not on a hard pull and the press of gear on the shaft is still tight. You say it grinds when trying 5th. Is this with the clutch released or disengaged? If you can push the clutch pedal down and shift to 5th and it pulls it would be a bottom shaft problem. Would think if the input shaft and constant mesh gear have teeth missing or bad bearings moving the gears apart you would hear bad noises when it stops moving.
One other possibility I can think of. Does the tractor have a aftermarket 9 speed transmission or had one partially removed?
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Today's Featured Article - Gatherin of the Orange - by Rick Nikolich. In July of 1998 I was talking to fellow Allis Chalmers collector Mike Schilling about the annual "Gathering of The Orange" AC show coming up in August of 1999. He got this wild idea that we should get a convoy of AC tractors and drive them from Charlotte, Michigan 105 miles to LaGrange, Indiana.
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