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stock stroke, high compression, good heads, and a big cam would get you there I'd think.

or you can cheat, drop a 440 stroke crank in there from your choice of stroker sources, (aftermarket that's already made for the 383/400 mains) and turn the 383 into a 426, 431, or 438 depending on how much you have to bore the cylinders. That, combined with compression, head flow, and cam, will get you 450-500 hp that is VERY streetable.

my 383 stroker was making over 500 lbs of torque at 3,000 rpm where the dyno started measuring, and it stayed at a nice flat 500 lbs through the RPM range, peaking at 535 at 3800, and made a peak of 505 hp. that's with the above combo--440 stroke, flat top pistons, eddy heads, comp's xe-275-hl hydraulic cam.

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for a street driver I'd follow this recipie...the smallish cam should have good streetability, tons of torque and good power to about 5500 RPM.

if you're buying a new crank, I'd go past the 3.75" stroke and into a 4.15" crank, if you can find a shelf piston for a 4.28" bore/4.15" stroke combo. would yield 478 cubes and probably 520-560 lb ft of torque, with about 500 HP

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Diamond has a piston for a 3.75 stroke using the std length B rod for a taller piston .

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Good call. Didn't know about those pistons. By my math that gives a 1.75"-ish CH. Not too tall; not too short. A cleaned up stock forged crank and maybe some new CCJ rods and you're into it pretty reasonably.