Engine building is a personal thing with most hot rodders,
Having come up around race boats, I tend to be more cautions, as a rod or other piece of shrapnel out the bottom can sink your high dollar boat fast.
If it were me . . . . I'd build a nice 383 which can give you 450 to 500HP all day long, and it'll do it with basically stock internals and a 2 bolt mains block, especially if you run closer to 450 than 500.
If it's a 4 bolt main, then I'd look at a Scat, (or similar) forged rotating assembly with some decent 8:1 forged pistons, aftermarket aluminum heads, and a 6-71 blower kit. You can easily hit your 500 target, probably closer to 550 and still be very streetable.
Either way, you'll want aluminum heads, hydraulic roller cam, and quality roller rockers. . . . Get good stuff, avoid the Chinese crap wherever you can, . . . If you're going to spend good money on a nice project, why would you want to bottle neck performance or take chances with reliability . . .