I understand the desire to go with a 440. My first car was a 1968 plain jane 318 Charger. I put in a 440 and made the car into an R/T clone. The car was more valuable and fun in that form for sure. However, I will say that I don’t feel bigger is always better. Bigger is perhaps a little too overdone in this hobby in my opinion. Bigger engine, bigger cam, bigger carb, bigger brakes, bigger exhaust, bigger tires, bigger, Bigger, BIGGER!
As others have said, it’s your car. Do as you please. Bust first, ask yourself, what do I want to do with this car? Race it? Set a land speed record with it? Have bragging rights for the fastest most powerful car in town? All the above? Well then, go 440 or better yet, a stroked 440.
Don’t get me wrong. I like Hemi Road Runners. I like A12 Road Runners. If I had the money I’d own one of each, but I have to say that when I see a 69 Road Runner where the owner swapped the 383 for a 440, original or not, my heart sinks a little bit. In my mind there is a certain nostalgic mystique that goes with a 383 Road Runner.
So if you just want something that runs well and has reasonable performance for a street driven car, perhaps a well thought out 383 build will suite your needs just fine. And maybe, you'd even be plesantly surprised?