Below is an image of my front jug from the EVO on my Fatboy. In the past month I've noticed oil seeping out of the side of the jug. I recently switched to synthetic Mobil 1 and am guessing I have to replace a gasket of some sort. Has anyone dealt with this problem before? Tough job? I might drop off the bike at a local shop for this one.

The bike holds oil, I still run it and just wipe it clean after each ride. I got the bike a year ago, and it didn't leak any oil except for a tiny seep from where the primary cover meets the engine block. I want to switch the oil for the engine, tranny, and primary to full synthetic and don't mind replacing gaskets if need be.

 

 

Drain the oil and go back to Dino oil. Synthetic isn't a good friend to a 20 year old motor.

 

First off you are better off posting questions about EVOs in the EVO section.
https://www.hdforums.com/forum/evo-classic-models-84/

That said there are 2 ways to fix your problem
1) Change back to Dyno oil
2) Replace your head and base gaskets with either Cometic or James steel gaskets.

If your committed to using synthetic then you need to use option 2

 

This is highly possible

Back when Synthetic got popular a friend with a fairly new Honda changed to all Synthetic.
Danged if he did not spring some leaks (even from one of the plugs).
Before I cracked her open I would go back to good old fashioned oil.

 

I used to run Castrol "high mileage" 20/50....one day I notice a "seep" from the rocker cover...

At some point by chance I noticed they had changed the "high mileage" to semi synthetic.

Next oil change went back to full dino...no more leak...

 

 

No. Just do it.

 

Head gasket is already compromised.
Yank the heads and replace with Cometic gaskets. Might as well do them both while you're in there.