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I know this is just rehashing most of the posts above but for a street bruiser with a set amount of money invested, and an equal build, in the engine the 440 will be the champ EVERY TIME.
EVEN is the engines make the same peak HP (which they wont)

Area under the curve!!!!!!!!!!!!!!!

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Contrary to your BELIEFS.... which HAVE some merit, SET COSTS are not part of this equation. YES, the 440 has MORE cubes which gives it a distinct COST advantage. There is less cash outlay and ingenuity to reach 500 hp. The 383, as I stated before, can reach this 500hp level, but due to the less cubes a "bit" more money spent in the right areas can net a VERY capable street/strip motor with great power. If it was a question of money spent or saved (main reason to go with the 440!!) then the 440 definitely GETS the nod. But
a 500hp 383 make cost a little more, but can net you excellent performance. You want to toss 'em
away, good, more for me to build and develop power on!!