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Hard to get into gear

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Agree - likely a belt stop/clutch adjustment issue. As a variable speed tractor wears over the years, the specific measurements given in the shop manual become more of a starting point, instead of a final, precise setting.

Start there, then verify that the belt stop is actually lightly grabbing the belt just enough to stop the belt from moving when you fully depress the clutch pedal. Verify this with the engine running, but DO NOT try to make any adjustments with it running. It may take a few attempts to get it adjusted just right.

The brake adjustment effects the clutch adjustment on these machines because both are controlled by the same pedal. The variable speed is much trickier to adjust than a normal 3 speed because of the long belt and big pulley sheaves...

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