Has the motor ever been refreshed? If not, now would be the time to do it and have the cylinder base trued.

 

Same goes for using Cometic gaskets.

 

Don't use the service manual with James gaskets, use the instructions that come with the gasket set.
That's some good advice right there....

 

I'm finally getting around to taking a closer look and fix this vehicle due to an unfortunate incident I had yesterday with my primary ride (2011 Ultra). Took a quick ride down the Smokey Mountains this past weekend to ride some of the awesome roads. Camped out at the Iron Horse Motorcycle Lodge. If you enjoy camping, this is the place to stay. Anyways, left Iron Horse around 9:30am for the 750 mile trip back to NJ. Around 9:30pm just as I cross into NJ from PA on I-78, a deer appeared out of nowhere right in my lane. Fortunately he was a small one and I hit him on the left side of my Ultra just as I was passing him. He took out my motolight, bent the engine guard, my left lower with glove box is completely missing and my gear shift lever was sheared off at the shaft. Luckily I didn't drop the bike, fall off or break a leg. I'm very lucky I wasn't injured since I was traveling at 60 mph and this could have been a very serious accident. Hell, I could have easily fallen and been run over by one of the many 18-wheelers that were running that evening.
I have a feeling it's going to take some time to get my Ultra sorted out with the insurance company and I'm already signed up for a 500 mile motorcycle tour this weekend and I have the Indiana Boogie (750 mile ride to get there) the following weekend.

So, I'm now forced to make sure my Fatboy is road worthy for some long trips, since it hasn't been used in sometime.

Checked oil level and primary fluid level, both looked good!
Transmission fluid level was low, about 7 ounces.
So, I'm thinking the leak I have is tranny fluid and as you mentioned, the tranny fluid is being thrown right at the base of the rear cylinder.

I also noticed a lot of fluid/oil on the belt and around the belt guard. Is this also pointing to a tranny leak? Which seal should I be looking at replacing? Any pointers or tips on how to proceed?
If it is a transmission leak, could I still use the bike for a long trip and check/refill the tranny oil say at various gas stops? I'm just afraid the oil will make it's way onto the rear tire and make for some interesting riding.

 

You should clean it up the best you can and ride it to see how much/bad the leak is. What kind of fluid running in tranny ?

 

HD Semi-Synthetic Transmision Lubricant, part number: 99891-84 (gallon)
I picked up two of these at the dealer when they had them on sale for $6.79, regularly priced $27.97

 

You might be able to determine whether the oil at the rear cylinder base is engine oil or transmission oil by the odor. Transmission (gear) oil has sulphur in it, giving it a distinguishing smell.

 

I was going to say service it and ride it, but then a light bulb came on. Trans leak!

93 model year, I think they still had the narrow hub pulley and skinny spacer in that year.
If so there is a good chance your lock screw has sheared off in the drive pulley.

Replace pulley with updated wide hub pulley, thick spacer, and matching seal.

If you ride it the pulley may come completely loose...

 

Hmmm.... I just noticed an inconsistency between my motorcycle owners manual and the motorcycle service manual.

According to my HD Motorcycle Owner's Manual, 1993

Transmission Lubrication
Remove the threaded filler plug, Clean dipstick, Screw dipstick filler plug back into hole. Remove dipstick and take reading.


According to my HD Service Manual, FX/Softail Models, 1993

Install the drain plug and fill the transmission with approximately 20 - 24 oz of HD Transmission Lubricant. or until the dipstick on the side cover filler plug shows FULL with motorcycle in level, upright position and the dipstick dipped. not screwed, into the fill hole.

When I recently checked the transmission fluid level, I did have the dipstick screwed in. I'm fairly certain in the past, I just had the dipstick dipped in.
This now explains a bit of the mystery to me. It seemed like a lost quite a bit more fluid than the 7 ounces I recently added. Now I'm certain it's tranny fluid I am leaking.

 

The best way to determine where it's coming from, if you can't tell, is to clean everything and keep checking under there after short rides to find the first new trickle.