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The sort of stuff you are bringing up needs to be verified in a handloading manual. .380 and 9mm use the same bullet so it's just a matter of velocity. The .357 Sig uses the same .355 bullet even though it says .357 in the name. A .357 bullet would most likely blow up the gun if fired in a .357 Sig. A 9mm and a .380 uses a .355 diameter bullet, but the 9mm is faster than a .38 special, so the 9mm can do more damage than a .357 size bullet going at a slower speed. OTOH, a .357 magnum goes faster than the 9mm, so it makes a BIG difference in damage.

The things to consider is the weight of the bullet vs the velocity of the bullet. A slow large bullet won't deform as much as a smaller faster bullet so the smaller faster bullet may do more damage than a slower heavier bullet. Most reloading manuals have a foot pounds chart in the back that will tell you the info you are seeking if you know the weight and speed of your cartridge.