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Any ideas before I tear back into the tranny?
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I'm away from my bike and service manuals so I cannot remember the correct terminology but here goes...
The first thing I'd double check would be the shifter pawl adjustment. The adjust screw should be located on the upper front-left of the tranny, with just a small amount of space to access it due to the inner primary. Around this allen screw should be about a 5/8" locknut. Can't recall.
Adjustment is made with the top tranny cover removed for observation. If no service manual is available I'd just google "harley shifter pawl adjustment". The info is out there. If the pawl isn't in the correct position it won't allow engagement of the cylindrical assembly that rotates and moves the forks to the correct positions. I had the same problem as you and had to experiment a little to find the sweet spot. 1-3 shifts were fine. 4 & 5 were difficult.