The bigger head will normally make more power, wether supercharged or normally aspirated, but it depends on the whole package, and what RPM you want to run.
Positive displacement superchargers make it less sensitive, as no matter what you do, it will make a lot of HP, but the big heads will still make more.
As I said earlier, there is a lot more to be considered, and volumes of air pumped and consumed, pressure and temperature changes, parasitic losses driving the supercharger, drive train stress, increased weight, impact on aerodynamics if it sits on top of the motor, fuel avaliability vs requirements.
When you supercharge, you increase the density not the velocity. This changes as the valve opens and the greater pressure difference then increases the velocity, but as the cylinder is charged, the velocity drops off, but the higher density is still there. This is a dynamic situation and not at all cut and dried.
If you want to pick my brain, make it easy and tell me the full story. I don't have time to play 40 questions.
You know, details of what type of raceing, their rules and regulations, type of fuel, type of engine, types of superchargers, type of car, expected life of engine, high or low budget, will you change cam and pistons and fuel supply to suite the supercharged motor etc etc etc.
Regards
pat