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I have a 2006 Polaris 500 and it won’t stop breaking the woodruff key I have tourqed it to spec about a million times and still breaks it. It will start and run but after u try to start it it a couple times it like stops cranking and breaks it.

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Without the key, does the flywheel sit tight;ly? Meaning if you put it on, and give it a shove, does it take a firm pull to pop it off? If not, the crank and or flywheel may be damaged. The correct fix is to replace the parts. However you can put a little valve grinding compound on the crank, pu the flywheel on and twist the flywheel back and forth.  Then clean off, apply some bluing to ensure full contact. This might resolve the mating issue. The key is not supposed to hold the flywheel, only locate it.

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