need advice resurrecting a muscle car

Is it possible the octane booster is past shelf life?  i hadnt thought of this, but i doubt many are using it anymore

 YES, EPA continually is changing the formulation of gasolines seasonally as well as regionally. the only real way to get the A/R ratio near what's needed is with an A/R monitor or an EGT gauge. You can guess and maybe get close. Are burnt valves or worse worth guessing? With the other changes that were made to the cam, intake and other things OEM setting are out the window. 

If the distributor has no mechanical advance, he WILL need vacuum advance, as it will either start and run at full retard, and not accellerate at all, or if manually advanced, self-destruct trying to crank at full advance.

Proper troubleshooting requires measuring here.  Measure timing, and observe advance and retard.  Shoot temps of each exhaust port and look for a cold port.  Lift a plug wire slightly when there's a miss and see if it clears (increasing a gap will clear carbon fouling of the plug).  If the distributor is suffering from stray spark, the ignition trigger coil may be getting false triggering.

More measurement of basic functions is necessary... get the facts FIRST.

B, or RB engine? I'd lose the electronic ignition for testing and go back to breaker points myself unless you have a known good replacement. Seen a lot of MSD and like competitors capacitive discharge ignition systems fail from both age, and/or lack of use. The capacitors break down over time and can yield many of the results you are experiencing. This can be exacerbated if the distributor shaft, or bushings are not in good condition.

Another problem with the 383 engine, (B series) and 440 engine, (RB series) if you have planed the heads and not addressed the intake manifold mounting flanges for angle correction is they will not hold intake gaskets long term. This is more pronounced on the 440 than 383. A high performance camshaft utilizing a lot of valve overlap makes a vacuum gauge a guestimate as they won't carry a steady 17" - 21" of vacuum at idle speed. 

1-8-4-3-6-5-7-2 is the standard firing order for the engines of the time and was very standard with exception of Ford who had to be different. 

I would be leaning on the ignition system for faults/failure from the writings. 

Easy way to know manifold vacuum from ported vacuum is any port above the throttle blades is Ported vacuum. (vacuum advance) Anything below the throttle blades is manifold vacuum. You could have a couple valves sticking from sitting. I'm not a snake oil guy, but a little Marvel Mystery oil added to the crankcase could help unstick a couple valves or lube up some lifters if that's what's causing the shake. A tight valve could cause the same issue. I installed a Demon Carb on the wifes 55' TBird a few years ago. That seems like a nice Carburetor. Adjusted up nicely as well. The main reason why I put that on is because of the the new style fuel bowl that runs 20 degrees cooler. The old T-Birds are like the old Corvettes. Tight engine boxes with not much air movement which builds under hood temps. The T-bird owners used to call the OEM Carb that was on them "tea pot" Carbs because they used to percolate all the time in the summer and then vapor lock. So far we haven't had that since we put the Demon Carb on.. Glad to see there's still a lot of folks that have the oldies but goodies still on the road today like myself. That's great that your son is interested in it. We need more of the younger generation into Antique Cars! 

Steve@B&B