I spoke to Jim this morning. Legend!
He suggested stay away from dreams of a large displacement motor, and focus on moving more air through it. I.e., supercharger.
He suggested a minimum wall thickness of .110". More than that, and you'll get into overheating issues.
He gave a few key details of one 392 build he did, which I believe is Robert Searles' motor.
1. IC392
2. SB400 stock bore pistons @4.125"
3. Dodge slant six rods.
4. Remove as much rotating mass as you can. They realized 20lbs removed! Much of it from going to a forged aluminum piston and removing the bob weights from the connecting rods.
5. Bush the small end of the rods for a BBC wrist pin.
6. Offset grind the crank. The realized a displacement of 427ci.
As for heads, he mentioned MPG Head Service and their CNC porting program for IH heads.
He did say years ago he had the chance to talk to the IH factory engine designer, and that the designer agreed they were raspy motors. The designer said the best numbers they ever saw, wee from putting 304SV head bowls in 392 heads, among other things. These were the heads used on the factory backed Baja racers. That's pretty extreme and sweet at the same time.
I'll call him again soon, and pick his brain.
Thank you Zaed!