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Probably buy new rings and have the cylinders re-honed is what I'm thinking depending on what we see when we open it up ... again.
I think there is a definite issue due to errors made during break in. I may have run the break in oil too long too???
The spot on the front plug seems to show a ring gap issues allow distinct blow by to create a defined burn line on the plug, and the rear just didn't seat proper and is the oil burner.
The Indy and me talked about the critical alignment in the rings and has used them before and felt they were a good choice. His method of the first start ups mimics the manual. Cautious, multiple heat cooling cycles before hitting the road.
I just read a good article on break in from another conversation here. I didn't follow these instruction.
Dude... these bikes aren't rocket science. Fill it up with Rotella, or HD 20w-50... it don't matter. Fire it up, check for leaks, put your lid on, and go ride the dang thing. No need for silly complicated break in procedures, goofy break in oils, or any mystical type of thing.
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