If you'll look inside the hole where the plug goes you will see an oil passage on the side of it. Screw a plug in too far and you will block it.
I don't usually run 'em, dad, son rivalry thing I think. But I like them real well too. They are beautiful motors and the more you know about them the more likable they become. This is good tech, There is a lot to know about nailheads, little quirks that most machinists never know. Nice to see someone actually taking the time to build one right.
I know this is an older post, but I love the engine build threads. Nice job on the nailhead, it's a beauty. I do have one comment regarding you grinding the oil galley plugs on your lathe. I've always been cautioned to never get grinding dust anywhere near my lathe, as it really accelerates the wear on the ways.
This is a good thread, can't learn enough about traditional engines, keep it going! Below is a pic of my 322, 54 Roadmaster Nailhead, presently in my avatar.