#1 you have to have the intended vehicles PURPOSE (goal) in mind to make the rational decision.
I agree. Build a engine ONCE. Going from 10.5:1 CR back down to 8.5:1 CR is not accomplished cheaply, and neither is going from OEM cast to 12.5:1 CR forged pistons.
To me....I approach this thread and wonder....."he HAS a 440, I do not know what chassis, but.....what exactly is the current running state, and what is the concrete goal"....your question is excessively vague for such a costly venture.
And too be blunt....the power capability and driver kinda streetability you want...IS Turbocharging.
This is me personally-
Because hmmmm do I want a 5.9L, maybe a bored & stroked out 6.2L, maybe skip the small blocks and go straight to 7.2L-440.??.....Nah I want a 5.9L that breathes like a 12.0L V8, SUPER kinda torque, and consumes fuel like a 5.9L v8 when I want it to....turbo(s).
To each thier own....and LOL....I just thought of something even funnier.....If you go Turbo, you can make your mind up AS YOU DRIVE.......Like "WOT....Forced induction!!!! - 10 psi BOOST....or part throttle.....No BOOST."
LOL....turbos are for the confused.