[REpozer]

I have tried several times to stop a leak in my primary cover shift shaft hole .
I've pulled the primary cover and tried to seat the metal shaft bushing against the cover on the inside.
Also repositioned the rubber shaft seal on the outside.
Leak always comes back.
  This should be simple , am I missing something silly here?

[ace.cafe]

Even though the primary on 5-speed Iron Barrels is slightly different, I think that the shift shaft arrangement is about the same.
Typically, if the bushing gets worn, the shaft gets out of the center of the seal, and then the lip of the seal cannot really seal it well.
Most likely, the bush needs to be replaced, or perhaps you can drill it, and press in a bushing liner with a close fit to the shaft, and make sure it's dead centered.

[REpozer]

Thanks Ace.
Would be worth a try and ordering/installing a new metal bushing.