I ran some Rotella T (now motorcycle approved) in my bike and neutral became impossible. I switched back to valvoline 20/50 for wet clutches, and within 20 - 30 miles neutral was a breeze again. In your case I would say maybe oil isn't the case, but it never hurts to try. My bike is a 550 so my clutch is a bit different than yours. Were I you, I would try some less invasive testing with oil before tearing things apart. I dont know about this countershaft o-ring fix. I have heard drilling the oiling system of the clutch can help, as well as replacing o-rings in the oil pump. Currently I am rebuilding my motor and amd replacing all O-rings, you'd be surprised how flat those O-rings can become over time. I dont know about replacing oil pump o-rings on a 500, but on a 550 its not that hard. I would maybe pull the clutch is an oil change fails. Make sure the clutch discs are worn past spec. If everything checks out ok, I would replace pump orings and make sure oil pressure is to spec (the light wont tell you that).