How easy to get 500 horsepower w/ stock stroke 440?

A gear vendors overdrive is not a transmission. You would have "a 440 with a good ol 727"

I understand that. But for how much they are, it would take a long time to re-coupe the cost in with fuel savings.

But if you select the right parts in the initial build to make the engine more efficient, it shouldn't cost that much more and there will be more power and better MPG. How much, I don't know yet.