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 - Oil Bath Air Filters - by Chris Pratt. Some of us grew up thinking that an air filter was a paper thing that allowed air to pass while trapping dirt particles of a particles of a certain size. What a surprise to open up your first old tractor's air filter case and find a can that appears to be filled with the scrap metal swept from around a machine shop metal lathe. To top that off, you have a cup with oil in it ("why would you want to lubricate your carburetor?"). On closer examination (and some reading in a AC D-14 service manual), I found out that this is a pretty ingenious method of cleaning the air in the tractor's intake tract.
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