You have received excellant advice on adjusting clutch and ta linkage.
Maybe I missed something in the post but it seems like you are having trouble shifting when there is pressure on the trans gears. Which in my opinion is normal. Similar to when park on a grade it is hard to shift.
When you release the brakes the tractor is free to roll slightly releasing the tension on the trans gears and then it shifts easily.
Both my 300U's shift great and the clutches do not slip on hard pulls. Yet both of them will not shift when stopped on a grade or against something and then I have to rock the tractor slightly and it shifts easily.
You may not need to adjust your clutch at all, experiment and see if you can figure out the circumstances that make it hard to shift.
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