Charging system troubleshooting

You got it. This schematic illustrates how I tested the VR yesterday. Bad wire connection - you mean with the jumper? I'm going to try to duplicate it again tonight.
Maybe - I was thinking more like the splice or connection when the second wire was added (by previous owner).

For example if either of these connections is loose.
upload_2019-7-14_21-28-58.png
I'm not familiar the "blue" VR.
Mopar Performance sold (sells?) blue painted electronic regulators. The one I mentioned was for alternators with one field terminal grounded. I'm pretty sure they also sold one for isolated brushed alternators like you have. Had the same triangular connector as a factory regulator.
The current VR on the car is a NAPA Echlin. Don't know if this makes a difference: the current VR has a smooth face; the two replacements I found (cheapo Chinese and an ACDelco) have a slight step-down on the face.
I haven't had to experiment with buying these. The most recent AC Delco item I bought was an alternator for my Wagoneer. QC was not there - would have flagged a major problem if this was a GM production item. parts store exhanged it and we got an older one that was fine. It's crap shoot out there.