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You're starting with the same cylinder heads that would make 400 hp. on a 440, so you know it'll flow enough air. Just have to spin it a little higher.
How much do you want to spend? Rebuild or just replacing parts? 906 heads or aluminum? What is the status of the engine now, stock, modified, in need of a rebuild?
Im guessing you have the stock iron intake. A used holley strip dominator or a dp4b if you want to go with the stock look can be had for cheap. headers are always a welcome upgrade for breathing. What distributor did the rebuild come with and what is the initial. A cam swap is always a help from the stock 208/221 cam. Something like a comp 274 if you have the piston clearance.
Not hard at all. Heck I built a mild 383 some years back for my Dart I had at the time and it ran very good for a mild 383. The Dart weighed about 3600lbs with me in it and it ran 12.31 @ 110 which I would say is a good 400 hp at the flywheel or more. It was a completely stock bottom end with 452 heads that we just blended the bowls and I cut for a true 9.5 comp. Had the old MP .484 cam on a 104 centerline and use an RPM intake with a 750 DP. The car had a 727 with a Turbo Action tight 10" conveter and 3.91 gears. I was shooting for a nice driver and high 12's so I was very pleased when it ended up running 12.30's on good days. If you build a stroker out of the 383 you can have a very strong eng. Ron