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Probably the first 15 minutes of driving the top speed is around 40. Yeah grades will kill your speed, welcome to 1950's power to weight ratios. You are probably right though, carb ignition timing etc has to be pretty close to perfect to get the raging 130 hp.
As far as “boggy”, the 302 doesn’t have a lot of azz under 2500 rpm. You can force high rpm shifts by using “hilly”. The 302 is ok with 3400 rpm all day, she’s screaming but that’s how uncle ran her back in the day.
Looks like 42 nd Infantry Division (New York National Guard), 2nd Battalion, 108th Infantry Regiment, Headquarters company, 85th truck assigned to company. Very storied history to this day. TP45 is of course tire pressure.
Maybe try this, drive the truck up against an immovable object like a tree, put in high range, engine a little over idle, and crawl under the truck and beat on the reduction unit with a sledgehammer. If you get killed doing this, sorry in advance.
How fast were you going when you did the "shift to high" trick? When it lets loose it will be a deafening bang. Removing and taking the transmission apart to fix this is no fun.