After I finally got my bike tuned and road a short 20 mile ride when I got home I noticed oil right around the back right rocker screw on the rear rocker. Upon further inspection I noticed a hair line crack that was the culprit. Any idea how this could of happend? Do I run the risk of damaging the motor if I ride with it cracked like this, it doesn't seem to be much oil? How much of a pain in the arss is replacing this, it looks pretty tight in there?

 

I don't know how it happened other than someone torquing the bolt too tight.
It's a bit tight getting the rear rocker cover out and back in but it can be done. I suggest removing the rear bolt on the gas tank, lifting the tank up and then wedge a piece of 2x4 between the back of the tank and frame. Better yet, is removing the tank and getting it out of the way.

You will need an INCH pounds torque wrench when you reinstall and a Motion Pro rocker box wrench comes in handy to get in and re-torque the bolts following the torque instructions in the Service Manual. Clearance with a socket on the torque wrench is an issue without the Motion Pro extension on the torque wrench.

Get your replacement outer rocker gaskets from Harley. Aftermarket rocker cover gaskets from James and Cometic have always caused me grief down the road. When you pick up the gaskets from Harley, also get new fiber gaskets that go under the bolt heads.

If you use the Motion Pro extension on the torque wrench, you'll need to recalculate the torque wrench settings. THIS SITE will let you calculate the torque settings based on your wrench length and the 3" extension the Motion Pro extension gives you.

I did both of my outer rocker gaskets this past week and it took 2 hours including removing/re-installing the gas tank.

 

What's weird is it came out of nowhere. I haven't been anywhere near that part of the bike. Maybe it just happened over time I'm not sure. Any risk in damaging if I ride untill I can get the part.

 

I doubt it, just keep an eye on the crack and your oil level, but Iwould be looking for another cover.

BTW, I've found the rear cover comes off easiest by sliding/working it out to the right side of the bike.

 

I replaced the rocker box cover tonight. It looks the rocker arm hit the cover causing the crack, what do you guys think? Is that even possible? There was no mark what so ever on the rocker arm.