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It wouldn't hurt to clean and tighten all of those bulkhead connections up.

?............

Download the '69 FSM at Mymopar.com............ https://mymopar.com/service-manuals/

Seems to me it's unnecessary for a 4 pin ECU on a '69, no? I'm thinking L1 being in the key "on/run" position and not getting voltage would be an issue to find out why not. This has voltage with key "on/run" and key "start" position? Other checks you might make..... Continuity for both...

4 pin ECU conversion wiring on my '69..................

Sooooooooo, What voltages are you getting to the two ballast leads in start and run positions?

Do the check on the Leads, NOT the resistor. From MP ...........

Mine is a single ballast but as I understand it, you should be getting battery voltage to the ballast from the ignition switch. Disconnect BOTH connectors at the ballast. Ign 2 connector (red) should have battery voltage with key in "start" position. Ign 1 connector (green) should have...

There's this if it can help rule out the dist....... https://www.forabodiesonly.com/mopar/ams/easy-electronic-distributor-check.205/

................and bulkhead connector.

Possibly "fish paper" such as this...

I use a large Craftsman blade screwdriver and an adjustable...... I can work it back and forth to get it to climb up for me. Some extra oil may help. If that don't cut it, off the pump.

Outside the box, you could take a few thousandths off the plug diameter.

I had several straight boot plug wires I had issues getting on in my Abody for lack of space. I ordered 90° boots but was sent straights. Here's #7 and a straight boot. Right up against the steering. Could not get it on until I lubed the boot and slid it up the wire. Got the connection made...

Some of the stuff I use. The shorty plug socket (w/o the rubber bushing) and box wrenches work pretty well for me. A 12 point deep socket can allow a bit of an angle for tighter plugs a 6 point won't get on. Careful though, too much angle and you can break the ceramic. A 3/8" drive fine tooth...

Some info here..... http://www.mopar1.us/electronic.html

Looks like a '75 but I have nothing earlier ..........

Might the SB vacuum advance be working in the wrong direction?

Maybe add a couple steel distributor base gaskets to space it up? (not an o-ring)