Sorry for the rambling post that follows; hope you can bear with it especially to the last paragraph, where a good candidate for the problem is mentioned:
Listened to the video and I don't think I would be chasing the ignition any more. I would only change the condenser one more time, and then run 2 more tests of the ignition system when it acts up again.
1. Use either a spark tester or set the gap at the end of the HV wire off of the coil to 1/4" from metal, crank, and see if the spark is a good blue color and jumps a gap of 1/4" or more in open air. If so, your cranking spark is fine.
2. When idling rough, place your voltmeter on the end of the ballast fed by the ignition switch and check to see if it stays steadily close to 12v to make sure the ignition switch and wiring to the ballast is not failing or erratic. The voltage may vary some with a rough idle due to the alternator output going up and down but should stay in the neighborhood of 12v.
You have done lots of proper work with the ignition system and your measured coil voltage is good, and all that you have done pretty much eliminates that. I think your time spent messing with the ignition allows an erratic fuel problem to come and go. The 'dieing while running on the road' and the suddenly erratic point to that or an erratic manifold leak.
Vacuum: When it wants to die on the road, does it run better if you open the throttle? That would point to a vacuum leak. Can't see what you have for vacuum connections, but this exact behavior can easily be caused by an erratic vacuum hose leak but that only shows up at idle or with the throttle near to the closed position.
As for fuel, I would put my #1 vote on a fuel issue; just because a lot of the fuel system parts are new is meaningless; new parts fail too. The 'start-idle-then die' sequence really sounds like the carb is full of fuel at first and it will idle long enough to empty the bowl and then die; it will act just like your video. Similarly, a leaking hose from the top of the tank to the main fuel line or from the fuel line to the pump, will suck in air and cause erratic operation at idle and when driving. And of course the fuel pump itself will do this if erratic. You mentioned Duralast for the distributor and if you are getting parts from the chain stores, a failing fuel pump out of the box is sadly not all that uncommon.
Tee a fuel guage into the line to the carb and see how that behaves when the car wants to die at idle. The pressure should be steady with maybe just a little pulsing; if erratic while running, then you have a fuel blockage, air leak into the lines, or a bad pump inlet valve. Then shut it off; the pressure should stay up for many minutes; if it drops after stopping the engine, then then the fuel pump's outlet valve is shakey/bad.
Also, is there any reason to think that the fuel pump's drive lever is not aligned right or the fuel pump is not set into the block right? The fact that you just replaced the timing chain and the fuel pump eccentric is right there makes me suspicious that the eccentric or pump is not installed right and is not moving the pump lever properly. Was there any thing odd about the eccentric? Did the keyway get lined up right? Again, a fuel pressure test is in order.
