Compression ratio question

[Caleb]

i have stock CR on my 350sbc now but im about to swap heads on my truck. so last night i was playing with some numbers and came out to 9.6:1 with a .041 head gasket and 10.3:1 with .015 gasket. They are aluminum heads im putting on and ive heard they had leeway for more compression on lower octane. so if you were me would you push higher compression or lower? and could i get away with 87 octane or would i have to go with 89 or 93? i get i should probably test a listen for pinging, but im worried that if it pings even during testing that it will break something. whats the best way to go about this?