Compression Ratio and Boost Query

Interesting. What you are saying is what I was thinking may be the case from my minimal turbo experience.

Just to be clear: My actual expectaions are 8-10 psi max @ 5800-6200 rpm with 8.5:1 compression.

I would like to avoid the O-ring approach.. but.. It is certainly a consideration, and likely necessary as you said at 14psi with that setup.
O ringing the decks is not necessary until you get really serious with cylinder pressure. It shouldn’t even be part of the conversation. An 8.5:1 318 on 10 psi will be fine with regular old felpro head gaskets if you can keep it out of detonation. If you want some insurance stud the decks and use MLS gaskets from cometic.