This has been an interesting thread, both from the standpoint of cylinder wear vs piston design and for the discussion or leakdown, or differential pressure, testing.
I'm not an expert on the leakdown testing issue, but do have some experience with the technique, so I'll add what I can to the discussion. I've been using a tester that I bought from an airplane supply house several decades ago. I don't know what the orifice is, but I suspect it is .040". I think that was pretty standard back in the day. I've done a fair number of measurements with it on Commando engines, both race and street, and my experience has been pretty much like Jim's, although I haven't done anything like the number of measurements he probably has. I pretty much only use it for troubleshooting if an engine isn't performing properly.
It appears that leakdown testing is kind of like dyno testing, in that you can't necessarily compare measurements unless both are done with the same instruments and procedures. Still, my experience is that a good race engine will show about 5% when fresh, and I don't worry about it until it gets past 10%. That may seem like a lot, and it probably is if it's from the valves. It it's the rings, and the bike still runs good, I'm assuming that the ring seal is better with combustion pressure behind the ring.
Keep the results coming Jim. The whole piston design subject is fascinating, short skirt/long skirt, high pin/low pin, best alloy, ring material/coating, piston coatings, ring type (Dykes, Total Seal, normal or thin, flat or barrel), clearance, bore coatings, and so on.
Ken