Brainstormin' 440 vs 5.9 ...

Put a LS in it.

:lol:

Well done.

What does the truck weigh?
You can get 450hp out of the 440 you have with some decent headwork and 500-525 lift cam. The carb needs to be big enough to feed it. Running a 750 will probably have 1-2" of vacuum at higher rpms, that will be a tell that it's not enough carb.

Just a wild guess 450hp/390rwhp at 4000# can run a 12.90/108 or so at a 1500DA. That's good hook and efficiency. Converter/hook is the key