Need some advice on some cylinder head gaskets

But with the bore size being .150 larger, am I asking for trouble?
No. But it would be advantageous to have the least amount of wasted space. Cometic gaskets….

How much quench are you gonna have running a thick head gasket to lower your compression ! You get to much quench you may run into a detonation problem, could tear up some pistons !!
Negative Sir. Timing is more of the issue at hand, not quench. He could run a flat top zero deck piston with a .030 head gasket at .010 more bore size than the cylinder and a closed 63cc head while adding boost.

Now the amount of boost could be limited due to timing limitations. If the timing could be taylored correctly, he could still run 15 lbs. of boost.

At this point of running boost, I, myself, would run a forged slug.