If its any consolation, three speeders can have the same problem. All sorts of things have been done in the past, including fitting a tap in the oil line. And yes, folk have driven off and forgotten to turn the oil feed back on.
Old engines though tend to survive, ball and roller races don't need that much oil, it's white metal bearings in modern engines that quickly suffer (don't know the technical details of the S&S engine).
Me, I'll stick with my total loss engine - the roads need a bit of lubrication...
Actually, most folk use catch tanks these days, oily roads are not terribly popular with motorbike riders. 
