440 what am I missing here?

Yep! I’m coming up with less pressure than you are showing using the average barometric pressure for your area today. But when I use the listed chamber volume of 74cc’s instead of 78 cc’s and err to a heavy factory deck cut on the block to 10.72, then I’m coming up with 10.4:1. That equates to 146 psi cranking pressure, so given the bleed down PRH mentioned I could see that as being pretty close. Now, for the sake of comparison, let’s advance the cam timing four degrees to 100 degrees ICL and intake closing of 68 degrees ABDC. now we have a cranking compression of 152 PSI. We need a much earlier intake closing event or shorter duration here to get the pressure up to acceptable levels with those gears and the tight converter.