Beautifully written Mr Max. I think you're dead on. If this o-ring was as problematic as some thought, it would be a known issue at Yamaha that they should have addressed. That reminds me of the starter clutch that they seemingly knew about but chose not to address for the entirety of gen 1 production. I want to believe that the starter clutch being ancillary in nature caused them to disregard it as a maintenance item. Oil starvation on the other hand is not maintenance-related, it can cause total engine failure. And by that logic, they would've fixed it if it was the o-ring was causing oil starvation/engine failure on a large scale(as you said).One thing I don't read about is engines blowing up on a regular basis due to lubrication failure.
That said, it's an easily preventable point of failure and I'll replace the o-ring for peace of mind. I love a cheap fix that brings more confidence in my machine!