I have tried to make sense of your post for a few minutes now. You are throwing out a ton of good info here. Are you saying that his dynamic compression ratio is too high for his setup. Therefore he needs to lower his compression? Yes - IMHO. That is why he is required to run a fuel additive and run conservative timing, but both aren't enough to actually fix the issue. Hughes engines should have known better than to advise him to run this camshaft with 10.5:1 static & cast iron heads. This would be an excellent combo with 9.5:1 static compression.
If static CR doesn't mean jack then how do you go about figuring out if you components work together on the dynamics CR side? I am planning out a 440 right now and haven't yet considered dynamic cr. Just static at 10.5 for pump gas. Google - dynamic compression ratio calculator. If you're running a modern aluminum head & chamber, 10.5:1 static isn't out of the question, as a general rule, you can get away with anywhere between 8.5-9:1 dynamic in most situations on 93-octane. With factory iron heads, 8.5:1 dynamic is probably out of the question on pump fuel. We don't have the luxury of an ECU pulling ignition timing and altering injector pulse width, every time it senses knock. So, in most cases, it's better to be conservative.