Perhaps it's sucking the fuel out past the feeler pin o-ring, but when vacuum is not applied it doesn't leak.
I can't see how a leaking headgasket would leak fuel into the sump, coolant maybe, but not fuel.
Andrew
Just for the sake of future reference, I think I have this problem figured out. In order to check for diesel being sucked through the aneroid vacuum line, I changed the oil and disconnected the vacuum line from the LDA on the injection pump. I replaced the t-fitting with a straight fitting so I could keep vacuum to operate brakes, climate control, etc. I capped the barb fitting on the pump. I had planned to drive the car for 1500-2000 miles, keeping tabs on the oil level along the way.
After 300-400 miles, I noticed that diesel was leaking out of the aneroid PAST THE RUBBER CAP on the barb fitting. When I removed the cap to see how much diesel leaked out, diesel fuel SQUIRTED OUT UNDER PRESSURE! This happened with the engine OFF.
I think it's obvious this is how diesel was getting into my oil. It was leaking past the aneroid feeler pin o-ring, into the aneroid, being sucked up through the vacuum line, into the vacuum pump, and from there was draining into the crankcase. Now to replace the o-ring in the aneroid...which looks like a pain in the ass. Any tips? Thanks for your help guys! ---Aaron