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My objective with his car is to have a reliable and fun competition car that is reasonably competitive. Now I am faced with more bills which wasn't the objective.
I know that feeling well. This is why the my Dolly has been retired from regular competition and I am now racing a more modern car, but I can assure you it also has its problems.
Your issue certainly sounds like an oil supply problem to the head. Check the jackshaft end float, if the keeper plate is worn excessively or the groove in the jackshaft is worn too much end float will restrict or stop oil flow to the head.
I will make a long story short. I have had a similar problem with a cylinder head, worn cam lobes, rocker etc. A another head was fitted but oil pressure remained low. Numerous oil pumps fitted and problem continued. Eventually oil cooler was removed and everything returned to normal.
My preferred oil is Penrite HPR15 (15w/60).
Good luck with the repairs.
Mark