Well, I fixed the broken wire for the one circuit, but same symptoms going on. I have definitely pinned this as another bad switch.
I looked up the wiring diagram floating around here that matched my setup closest. I also dissected my original ignition switch, and was able to verify all the contacts in fact matched the diagram. With this, it was off to do some voltage drop tests at the switch itself with it still plugged in.
The first test was jumping pin 50 to pin 30 with the key in pos2. The car started as expected. Next, after studying my dissected switch and diagram, I determined that 15R (labeled as just 15 on my switches) was the terminal that should maintain power with key position 2 and the start position.
Now I decided to test voltage on that terminal, with the key in pos2 and start. In pos2, I read battery voltage. Now while cranking, it dropped to around 9-10v.
Not fully ready to condemn the switch at this point, I decided to check voltage at pin 30. Again, I saw battery voltage. While cranking, it dropped 1.2v, which is reasonable on an old car with old wiring. Battery voltage is 12.4v, and cranking dropped to 11.2.
At this point, again, I'm ready to condemn the switch. I made sure all the connectors were tight for the wires, and none of them were in bad condition at all.
One thing to note, I tried repairing my original switch, but it just isn't taking. With the switch disassembled, and the rotating cam that moves the contacts removed, I was able to clean all contacts (non looked bad by eye), and bend the fixed side of the contacts outwards to ensure good contact when the cam isn't pushing the contact open. After many failed attempts, I decided to disassemble it again, and check continuity directly from the center power part of all contacts (attached to pin 30) and the terminal plug itself. Even with the contacts physically closed, my resistance readings weren't great. I tried pressing the contact more closed, with no change. I then pressed the contact tab towards the terminal connector, and that's why I noticed a better resistance reading. It seems the switch has worn/gotten dirty where the tab of the contact actually attaches to the terminal connector where the wiring harness plugs in
To sum it up, it seems that there is a possible ignition switch failure that cannot be seen or repaired. Even if you think it's fixed, it will probably be questionable at best for how long it lasts. Not worth the trouble for how awkward it is to remove the switch.