I guess this is all for naught as I stripped the drain plug threads while "removing" the plug to drain the oil. Super. The old crush washer is pristine, though
Bummer. How did you strip the plug during removal? I've only ever heard of stripping the plug from over tightening.
For what it's worth, those crush washers can last a very long time. I used the original washer that came with my bike for about 8-9 years before it started to slowly leak. Then I bought a new one with the intent to reuse it, but after the second oil change it started to leak. Now I change it every time just in case.
Like Johnny said – the rounded side touching the pan.