440 power gains/ aluminum head advantages?

Your information delivery has been a bit convoluted and difficult to follow. I'll try to summerize:

440 w/ 6 pack pistons in an A Body
9.1 sec. @ 80 mph (about 13.80 @ 100 mph - 1/4 mi.)
2.0 sec. - 60 ft.
9.5:1 CR
160 psi cranking pressure
13 on the AF gauge @ WOT
Headers
292/.505" Mega cam
3500 stall convertor
4.56 gears

I'm guessing your race weight is 3700 lbs - Do you know for sure?
I don't think you said much regarding the head work. There can be big power difference between well prepared stock heads and poorly prepared stock heads.
Is the track times with, or without mufflers?

Your car is off everywhere. You should be trapping at 87-ish (109-ish 1/4 mi) in decent air. I call that a missing 80-100 hp. Your 60 ft is crazy too. I would think a stock 318, 4.56 gear, and 3500 convertor would give a 1.8 60 ft. I think you have one or two items that are way wrong hurting you on both ends of the track.

My thoughts:
Your convertor could be junk.

Your symptoms are very much like fuel starvation, but your AF ratio suggests that this not the problem. Gauges can be wrong. I suggest that you put a fuel pressure gauge tap located near the carb, and monitor your fuel pressure at WOT. If you have 3-3.5 at the carb at WOT, you're fine.

If you have mufflers, remove them or replace them. Mufflers at your power level really won't hurt you, but an internally failed muffler will kill power.

You have wiped cam lobes.

Spark plug wires are crossed.

Maybe post your time slips.