What I think it is:

The leak looks to be the quad seal between the input and output shaft.

The debris on the shaft spline looks like just grunge (oil and dirt) from dis-assembly.

 

Yeah I checked the splines r good. How's that seal get changed? Still have to pull the gear set?

 

And I was throwing around the idea of upgrading to a primo 6 speed builders kit. Do U have to take off the transmission or can u do swap that on the bike?

 

You can do it on the bike, leaving the housing intact.

Definitely looks like the 5th gear mainshaft and quad seal need replacing. How many miles on the bike? According to the mainshaft it indicates that you ride hard.

If your on a tight budget this builders kit will do pretty good. I'm running the complete Ultima 6 speed trans and it's holding up pretty good. The only problem I have had is the shift pawl spring broke. It can handle 100/100... I can attest to that...

http://www.ebay.com/itm/ULTIMA-6-SPE...-/361325024688

 

My bike is a 89. I would need 91 and up primary drive to use the 6spd builders kits. All I need is a 91 and up complete clutch with the same tooth count and then I can use the same chain and compensating sprocket. Right?

 

The quad seal is picked out with any tool you can snag it with and simply slides back in place.

I'd like to see a photo of the Inner Primary Bearing (IPB) race surface of this 2 piece bearing, looking for improper wear. Setting the race on the main shaft can be tricky. Too far in toward the tranny and it allows the main shaft to wobble and takes out the bearing race surface. This allows the Inner Primary seal to leak and become damaged. This can also allow the quad seal to tear itself up. If you use the stock 2 piece IPB there is a Loctite product designed for securing the race in the correct position on the main shaft. This keeps it from shifting (walking) on the shaft which is a common problem. ALSO: The stock seal often gets put in backwards. It holds the primary oil in it's case and needs to be positioned to seal in reverse of how you'd think it should be put in.

Baker makes a single piece bearing that is an upgrade. The bearing mounts in the inner primary and comes with a required seal that is very durable. This prevents the race from moving up the shaft, become displaced and allowing the main shaft to wobble and leak. It mentions it's only needed for high horse power builds but it solves an issue that occurs regularly on all older Harley primaries.

Typically the IPB seals leaks while running and allows several drips of primary fluid to hit the ground while parked. The quad seal allows a large amount of transmission oil to run out while parked on the side stand. While this is all apart replace all seals.

Yes you can strip out the gears, bearings and seals while the tranny is still in the bike once you strip off the primary, exhaust, starter, etc. Truth be told the cost of adding a 6th speed kit is expensive compared to the end benefit. On your ride you'd need to be going at least 65mph or more to make it useful. If you travel a lot using speeds above 70 and holding constant on flat land you could see a small savings in gas.

 

That's some awesome info. Thanks.
The race is pressed on the shaft, right? How is it removed? It needs to be?
So the race has to be taken off, then use a pick to get the old seal off and then slide the new one on....that sound right?

No leaks from the primary

 

I think you can use one of these to pull the race


If you do pull it I agree with Johnny about going back with the Baker IPB.

 

I def will. Thanks for the help

 

The quad seal is just a oring? And is this the baker bearing and seal I need
http://www.amazon.com/Baker-High-Torque-Bearing-189-56/dp/B000TYLUN8