I think I remember reading in the instructions for the pump that said you have to use the included larger o-ring and not a standard one.

Would the motor being tilted forward make a difference? I have my back legs on the run stand a little high right now so the engine actually tilts forward a bit, which in mind should help prevent draining the line.

Cab-do you have any pictures of your homemade gaskets?
What material are you using to make them?

I don’t mind making gaskets, I actually made some .015 intake gaskets for this motor-the Fel-pro material is like $6.00 on Amazon.

At this point I am going to pull the line off the pump to see if I have oil in the line. How much oil should be there? Is it a go-no go situation, where if there is any oil there, then it has to be an air leak situation with the pump?

I have a brand new meiling high volume pump sitting on the shelf, so I would be tempted to bolt it on and give it a try. My only issue there is that the Milodon pump cover (top port) interferes with my Schumaker mounts, which is why I bought the Milodon pump and shaft to start with, plus I hate the idea of having bought $600 of oil pump only to not have it work ($400 pump/$200 shaft).