Reply to catsilver:
The main flywheel housing is, or should be dry on a D7 of this vintage, take the cover off and look inside.
Yes the master clutch should be dry, and depending on the SN it might even be open. Mine is. I think I would do the following.
Remove the plug from the pony clutch, make sure the Diesel oil is at the proper level, start the Diesel then drain the pony oil. They don’t hold much, then you could observe the volume of oil entering the pony crankcase. If there’s no oil dripping from the Clutch then you’d know you have a hole in the block of some sort.
Perhaps it’s a block repair from the past that’s failed. Keep us posted whatever you find.
Good luck
Bruce P.