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Just a guess, but... the shifter rod linkage joints & bushings could have been worn too much?
A firm, intentional shift should engage the gears without issues. Sometimes the synchros take a little wearing in, but they are usually pretty darn good when it comes to making sure that gears are smoothly engaged. The V-shaped teeth sometimes could have little dulling/pitting on the tip that could cause some hesitation. Maybe regular oil changes might keep the surfaces clean for friction-free sliding
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