I still have my original drain plug and this morning I was very tempted to put it back because I don't remember it dripping oil and I used it many times to check the oil level, but I changed my mind as the one I bought last year was a stainless one from Barleycorn Engineering - and I couldn't believe it wouldn't be right from Barleycorn, so I compared the two and both were identical length. Your right about the Dowty washer John, it is twice as thick as a fibre one. I even considered that but I didn't think a mm would make much difference and, of course, at the time I was only concerned with a drip of oil from the plug and completely unaware of the forthcoming oil level disparity.
At one time I would definitely have removed the chain case just to find out, but with a sidecar attached it's not such a straightforward job anymore and I can't think of another reason for it.
Rog.