What shape is the short block now? I agree it may not be the best bang for the buck to change pistons.
No way I’d run under a 750 carb on a 440. I won’t run less than that on a 383 either. Run a small carb back to back on either engine and then tell me which one you’d use. Once you feel the power you won’t run a small carb again.
A performer rpm is the best intake I’ve found for a street effort and it did great on smogger low comp 440s I had.
I agree the factory 375 hp cam is likely on target or is at least the outer limit on a truck build.