Choosing pistons

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Give's you an approximation of "boosted" compression ratio.

Aside from that. There's lots you can do to run boost with higher compression ratios on pump gas. Less timing. Keep it under certain RPM. Improved spark. Boost retard. Detune. Etc etc. But honestly these are all "band-aids". And are done to make a race gas engine run on pump gas, usually done by the racer guys who wanna take the car out around the town once and a while. An engine designed for race gas and detuned for pump gas WILL make less power than an engine designed for max effort on pump gas.

You mention you will run "large" combustion chamber heads. By "large" do you mean open? Open compression chambers actually INCREASE your chance of detonation. A closed combustion chamber only allows the combustion itself to occur in one controlled spot. Open chambers can have combustion occur in two or more spots. Especially if they are prone to hot spots. This is detonation.

Intercooler is a great way to reduce intake charge temp. Which will help you run more boost on pump gas. The cooler everything enters the chamber. The better.

I wouldn't run too thick a head gasket to take away compression. The thicker the gasket the better the chance of blowing it out. Dish pistons/pistons below deck are better, a combination of the two is best. Ideally you want to create a closed combustion chamber with the CR you want, while still having good quench and head gasket size. If that makes sense. For a headgasket look at something like a cometic. They make custom metal gaskets that hold up well to boost.