That's funny. The one who this had happened to is a mechanic and was once a large Chevrolet Dealership service manager. He can fix anything including his own motorcycles and I was just passing on what had occurred.

 

As promised reporting back. This turned out to be just a combination of slop in various parts of the shift linkage assembly and a clutch adjustment. Harley sells a complete shift linkage for $20 if you just want the plain rod and nothing custom.
Special thanks to ScrmnVtwins. I never knew about that spring adjustment.

Thanks All!

 

Just a note about the later 5 speed units...

2001 and later 5 speed boxes do not have an adjustment for the shifter pawl. Instead, there is a detent arm and roller that centers the shifter drum into position.

If there is a problem with the detent arm/roller/spring, the shifting can exhibit the same problems as an out of adjustment shifter pawl.