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Hello RapidRobert. Yes, I did get oil to both heads.
Is there a need to first "prime" the tubing with oil to remove the air from the line to get accurate oil pressure readings?

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No, you will see bubbles in any clear tubing for oil pressure or low fuel pressure tubing, air compress and pushes like it is a soild when compressed Did you buy a standard oil pump for a stock 383 or did you buy HP or high volume oil pump that fits all BB Mopars? the HP or high volume will have a high pressure bypass spring in them the stock non HP pumps won't I belive in and follow the ten pounds per thousand RPM rule when the oil is hot, if it has ten lbs or more at 1000 RPM and 20 lbs above 2000 RPM and so on your good in my book My last pump gas 518 C.I. 400 block stroker motor had 18 lbs at 850 RPM idling in gear with a solid roller cam that oiled the rockers full time with 5W20 wt oil at or above 180 F It worked fine with no issues at all It would have 65 to 70 lbs idling at start up depedning on the outside air temps at start up, IE oil temps in the motor The hotter the oil got the lower the idle oil pressure went EDITED, I reread your first post, a stock pump should not keep the same pressure all the time, it should vary like any and every other oil pump out there Me thinks it is time to try another oil pressure gauge I had a situation on a old M.W. car I bought that had set for long time before I bought it, I tried to prime it and the oil pressure gauge show nothing on it, I ended up removing the small copper oil ressure line from the block and found that it had a piece of thick gease blocking the small line, it definitily had pressure to the line before by having the drill motor slow down when the oil pump picked the oil up from the pan, it shot oil out two or three feet from the back of the block with the line disconnected IHTHs