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Your drain plug is completely normal for one coming from a racing situation. Gear changes etc create the slivers such as you have. You are ok on oil and how often you are changing it. THe only other thing I would do is mix off race gas 50/50 or run 110 VP ( or equivalent ) straight. SM stress teh engine like nothing else and a good fuel quality will eliminate any detonation, audible or inaudible, which will be the demise of your mainbrgs. My buddies ran a 650 ice racing, 5 - 6 hr events with no metal on the plug that relates to main brg failure.
About the cam chain, can't help there, but I do know that the extention of the tensioner relates to chain length. So when teh bike was brand new it may have been out 10 clicks, and once broke in, now is 11. Buy a new one, replace it, and see where it is on the tensioner, then you know. Why is the head coming off?