Welcome to Steel Soldiers and 302 troubleshooting. I got 4 of them started so I have all kinds of ideas that usually don't work but I maintain enthusiasm and that's how you beat these trucks.
Troubleshooting the problem should start at top dead centre and being sure the distributor is in the position as outlined in ....the book.... Did you check out the Tech Manuals here on Steel Soldiers or do you have access to the TM's?
There is a section in 9-8024 page 217 that walks you through the steps for the 302.
https://www.steelsoldiers.com/forumdisplay.php?118-Korean-War-to-VietNam-War-Vehicles-TMs
I can't say I've had the problem you're describing so couldn't tell you if the distributor can 'skip' a tooth, I don't see how.
Fuel flow with the specified 3-5 lbs doesn't seem to be an issue for these engines either because our 'new starts' usually get fed from a Jerry can hanging on the mirror. The inline filter screen in the carb got me once but I'm guessing you've eliminated fuel as a problem.
Run through that ignition timing trouble shooting section and eliminate the dist location as a problem......If you add your province in your location line it'll tell folks where to bring extra tools to help.
Welcome aboard!