I've never tried this, but in theory it should work to tell you if your oil pump is circulating oil.
Disable the engine from actually starting. Disconnect the oil gauge line, drop the end into a container, then crank the engine. If oil shoots out, your pump is pumping. It may take a little time to flow if your oil filter isn't filled up yet.
Each starter has its own tolerance to over cranking. I've killed an MZ4113 6v starter installed in a 12v system after on-and-off consistent cranking for about a half hour. I have one of the modern high torque starters on Rachel's 3A...and I doubt I could ever kill that off.