[Desertwndrr]

Where exactly is the leak? Can you take a detailed photo of the leak itself and not just one of the disassembled bike. Seals don't just leak without reason. There may be a burr at the sealing area. The shaft that is leaking may be out of round or have a wobble in it as well. Meaning that the seal is failing over time, not because of a bad seal, but because of a bad shaft or bearing. It could seal initially but wear out quickly. Replacing seals would be a temporary fix until the real issue is addressed.

 

[Desertwndrr]

Sounds to me like it's an inner primary input seal for the mainshaft of the transmission. Have them replace the seal and check the runout before they assemble it. I'd also replace the bearing and race just as preventative measure. I doubt that it's the starter o-ring as that doesn't move. The race could have a burr or even a microscopic edge that is tearing up the seals.

I doubt that it is the transmission seal because the drive sprocket and transmission look dry.

 

[Desertwndrr]

I must admit it is sad that I truly believe half of you reading this could fix this issue for the cost of parts and a case of beer, yet I cant pay the HD dealer $70 an hour to fix it properly, 3 times!

I don't even charge the beer.