Cleaned up the oily mess and the 40210-85D Transmission Sprocket Kit that I ordered finally arrived. Took a couple pictures of the original sprocket and the updated sprocket so that people can see the differences. The updated sprocket has more spline area. You should also be able to see the differences in the sprocket spacer in the pictures. Notice the slight grove cut into my sprocket spacer by the main drive gear large (outer) oil seal.
Next step is to replace the transmission seals. Might not get to that till after the Labor Day holiday.

 

Looking good, Smart move on the pulley update.....

 

Had a short window of free time yesterday, so I thought I'd try and remove the shifter shaft seal. Drilled two small holes in the seal and screwed in a pair of wood screws. Tried to pull the seal using pliers in both hands. The seal wouldn't move. Read on this forum how some people made their own shifter shaft seal puller, so I thought I'd try that route next.

Parts:
(1) Flat Bar Plain Steel, 1" x 1/8" x 2-1/2"
(1) 5/16-18 x 1-1/2" bolt
(2) #6 x 1-1/2" wood screws

a) use 17/64" drill bit and drill a hole on the flat bar, centered
b) use a 9/64" drill bit and drill two more holes, one on each side of the above previously drilled hole.
c) tap the larger hole for the 5/16-18 bolt

TIP: use a smaller drill bit first and work up to the larger drill bit size.

Used the above puller and the seal came right out!
I tried to be as careful as possible, but it looks like I nicked the inside of the seal with the tip of the wood screw. I don't think this should be an issue. Can someone with more experience please comment?

 

Made a little more progress today, unfortunately when I'm not familiar with a procedure, I work at the speed of a turtle. I'm lucky in that I'm not rushed for time since I do have another bike I've been riding.

Removed the mainshaft bearing race, which actually gave me a bit of trouble. The race didn't walk on the mainshaft, but when I tried to remove the race using George's Garage mainshaft bearing race tool (# 620060), the mainshaft would turn when I was turning the threaded rod. I lubed up the hardened tip/anvil with some oil and the race easily came off the shaft. I believe the friction between the anvil and mainshaft was causing the mainshaft to spin.

Also removed the mainshaft/main drive gear seal (small seal). I wasn't exactly sure how to do this, so I searched through the forum and found various suggestions which included:
use screwdriver
use picks
use sheet metal screws

I tried using some picks and I wasn't getting anywhere. I didn't have any small sheet metal screws and the metal ring on that seal is very small. Not sure I would feel comfortable using a sheet metal screw for this particular seal.

Then I remembered back in 2014, I ordered the Fix My Hog Touring Rear Belt Replacement DVD. Looking at the chapter topics covered in the DVD, they show seal removal. I watched the DVD, and they show using a screwdriver to remove the seal.
I take out my Craftsman 1/4" flat blade screwdriver, tap the seal a few times with my hammer, and the seal moved enough that I could pry it out with a small flat blade screwdriver. Total time to actually remove the seal, under two minutes! The attached picture shows what the seal looked like after I tapped it a few times.

https://www.fixmyhog.com/product/tou...placement-dvd/

 

Removed the main drive gear (large, outer) seal today. I tried to remove this seal the same way I removed the mainshaft seal, by using a screwdriver. Unfortunately, that method wasn't working for me. I ended up just drilling into the seal and using a Craftsman seal puller. As careful as I tried to be drilling into the seal, I did slightly nick the retaining ring under the seal.

I then lubricated the quad seal with transmission fluid and placed it on the main drive gear. Next I lubricated the main drive gear (large, outer) seal with transmission fluid and slide it onto the sprocket spacer. I then slide the spacer and seal onto the main drive gear with the seal just touching the transmission case. Using the specialty tool, I tapped the seal into place.

Next I lubricated the Cometic shifter shaft seal and installed that using the specialty tool.

I do have one issue that has me a bit baffled. It looks like the shifter shaft has shifted somewhat to the right side, since I'm not seeing the indent for the retaining ring. Does this shaft have some play and can I just "pull" it towards the left side?

Picture Legend:
Pic 1: Main drive gear (large, outer) seal removed
Pic 2: George's Garage large seal installer tool (along with the handle)
Pic 3: New main drive gear (large, outer) seal installed
Pic 4: George's Garage shifter shaft seal installer tool
Pic 5: New Cometic shifter shaft seal installed, but retaining ring indent isn't visible (help)

One minor detail concerning the large seal installation tool from George's Garage. Since my bike is a 1993, it has the older version of the pulley, and I went with the updated transmission sprocket kit which includes an updated pulley, sprocket spacer, seal, lockplate, etc.
It seems as though the tool is designed with the new sprocket spacer in mind. I don't think the tool would work properly if you used it to install the large seal with the older version of the sprocket spacer as one assembly. You'd be able to use the tool to install the large seal, but as a second step you would need to install the sprocket spacer. With the updated sprocket spacer, everything is installed in one step.