MainePorsche

Section in Dark Red - This sounds like a Light Relay issue. You could remove it, dissect it, and look for and repair the fault or you could get a new one.

Section in Dark Green - (1) At this time when you manually crank the headlights, is the Left light housing hitting or getting caught on the fender aperture ? (2) Are the two nuts loose on the actuator bar as spoken of previously ?

Regarding the un-united movement of the light housings we need to know these answers first before getting to the next order of business. You could jump a little bit ahead by removing the E/C clips and removing the motor linkage connector bar. This will allow you to freely move the actuator bar up and down by hand to really get a feel for the unison of motion, and to see which one is really 'disconnected' from its proper orientation. BE CAREFUL WITH THIS. THE LIGHT HOUSINGS WILL WANT TO FALL TO GRAVITY AND THE TORQUE IS STRONG.

Add: Also detach the cylindrical headlight motor harness which sits above the motor. You don't need this attached when manually testing the movement and seating.

MainePorsche

As we suspect it is your Left headlight, There are some places to look. First there is a 10 mm bolt lateral to the end of the actuator bar against the fender wall. This bolt is for your North-South adjustment of the headlight housing in its 'bed'. This bolt also holds the plastic housing (on the wheel well side) that is attached to the driving arm of the actuator bar. If this bolt (and housing) has play, your driver arm may not rotate as it should.
Another place to examine is in the Left wheel well at the union of the driver arm to the headlight housing itself. There are several areas here that can have defect in the union of the swivel plate to the driver arm.

Added: A pic of the driver arm's union with the swivel plate.