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Did he ever run the 383 with open exhaust? Most likely the 383 would not pick up as much. Some of these guys that think a 383 is a better motor than a 440 are off base. Your buddy made the right move. Dollar for dollar the 440 will out run the 383.
The exhaust is what is restricting your 440. The 440 is exhaling more than the 383.
I have full 3 " exhaust on my 850 horse Cuda and uncapped I only pick up less than a tenth.
If he wants to run through the exhaust he should start by upgrading the exhaust.
By the way I am running Magnaflow mufflers. They are straight through.

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really hard to say why either motor dont/didnt run,
for the straight across trade he did no he would run really close,
the 383 had compression, yes lighter , ,wether it 5# or 500 #
the addiadge was you could take 20 # battery out of the front of the car, take it put it in the back and thus lose 100# out of the car,
(rumor)
he used the same came heads carb, i have done this with not much pickup for the work involved.
now he can work on the combo he has , yes to me that combo should be mid 11 car, , that being said,, the 383 should be real close as well
i have done this deed, several times only to be disapointed at the end result,
did the exact thing when i ran small blocks , took out 360 270 h comp cam 8.5 ccp , put in realy swell 340, 10.1 nice pistons , warmed up heads solid cam ld 340 intake race gas the whole deal,
didnt pick up squate, ran it tune it, sold it , put 360 back in changed intake from the 340, ran faster , everyone said the 340 would flat out run that stock 360 didnt wouldnt , couldnt ,
why idono,
as for this poster , wish you the best, hope you do see that 12.0 11.90 ticket, or faster
good luck, dennis