It's real nice to see everything on one thread instead of adding a new thread for each challenge. You're much easier to find all on one thread.
Solve the fuel pressure question with a regulator and gauge. If you didn't need one before it's odd it could be a problem unless there's a new restriction after the tank and before the carb. It's just another toy to help read and regulate the truck. I could dial pressure up to around 6 and eventually dial it back to 3.5 psi where the truck seemed happy.

I don't know much but I know it's not the timing chain. It's direct gear drive from crank to cam. Many timing gears have been aluminum so I guess it's conceivable a tooth could break but your symptoms don't sound timing related. .........
..........as I'm typing something else popped into the cranium. Maybe those mechanic brains can help us out here on timing advance and if the governor lines around the back of the engine would cause his symptoms.
After pulling the floor pan, many of the trucks had damaged lines around the back of the engine. It appears the floor pan can rub through over time. After going through and eliminating other possibilities, checking sensitive rubber for cracks and leaks is always a good plan.
It's an easy job to pull the floor pan and get a look at the 2 lines from the carb, around the back of the engine, to the distributor. Most are metal then adapt into a rubber hose to flex into the distributor.
Many of those rubber lines disintegrated when we were pulling distributors out of 'take-out' engines. The connection on one line is a little tough to get at and you typically need two small wrenches in there to crack the lines. It's easier with the oil bath monster filter out of the way but those lines can be inspected with the floor pan off.

It's just one other thing that can be checked fairly easy, it's a one man job and gives a guy a chance to clean things up so they stay cool.
Compression checks can also be a one man job that gives you a health status on the squeeze part of the suck, bang and blow engine sequence.
I was parked beside a pretty rare jeep one time that had some real nice paint and canvas on it. The NEW rule was never to park on the exhaust side of a deuce because they may spit black soot on start up. We found out that windex helps to remove soot off paint and canvas.
It's good to find that out early because one never knows when a Sentimental Journey might show up and we do not want to get soot on our bomber.
