273 Stock & Elec ign questions

The male hex end extends clear through the oil pump. It souldn't seperate from the pump when lifting just enough to skip a tooth. If it did seperate you might have to rotate the engine just enough to get it back in the pump.
If you'll start with #1 rotor to plug wire while the advance servo is square with the block you should have plenty of rotation space to get the timing set right.

I know the dual points and pickups are in different positions on the distributor shaft but I'm not sure how that relates to the rotors position.
Just to know and say "yeah we looked", Lift both rotors and check the drive dog inside. I've seen that bit of plastic sheared before.