If you work in big city trauma centers it is not uncommon for someone to come in with a bullet hole on both sides. For handgun bullet wounds, it is usually possible to tell which is the entrance wound and which is the exit, even if the victim can't tell you because they are unconscious or dead. But it might require some fairly careful examination to do so.
As for human entry and exit wounds one has to remember that the skin is very elastic. Thank goodness it is or else many of us would look even more hideous than we already do. The high elastin content of skin means that it will usually stretch around a penetrating projectile and then retract some as the projectile passes through. Muscle and other soft human tissues are also somewhat elastic but to a lesser degree than skin.
According to Dr Gary Roberts, who knows a thing or two about about ballistics, the typical quality 9mm hollowpoint defensive handgun round will typically expand to around .60 caliber (.60" diameter), a .40 cal S&W round will expand to around .65 caliber, and a .45 cal ACP to around .70 caliber. Full expansion usually occurs within the first few inches of penetration.
If one simplifies and assumes immediate and full expansion on impact, then the volume of the permanent wound channel is estimated by the volume of a cylinder which is Pi x radius squared x length where length is the depth of penetration. So after full expansion a 9mm JHP round will damage .28 cubic inch (ci) of tissue per inch of penetration, a .40 caliber .33 ci per inch, and a .45 caliber ACP .38 ci per inch.
Assuming a 9mm round that penetrates 14", a .40 caliber that penetrates 12" and a .45 caliber that penetrates 10.5" they will all damage or destroy around 4 cubic inches of tissue. Another way of looking at this is that assuming all good hits with full expansion and 12 inches of penetration for all, 6 hits with 9mm is roughly equal to 5 hits with .40 caliber, which is roughly equal to 4 hits with .45 cal ACP. So in terms of volume of tissue destroyed and assuming equal depth of penetration, if you can achieve 6 solid hits with 9mm in the same time you can achieve 4 with .45 cal ACP, or 5 with .40 caliber, you will be roughly equal in terms of tissue damage.
But there is another factor that comes into play since the human body is not homogenous like ballistic gel. Some human tissue is vastly more important for survival than others, brain as opposed to skeletal muscle, for example. Also, even though a 9 mm round that penetrates 12" might destroy no more tissue than the .45 caliber that penetrates 10.5", that extra 1.5" of penetration significantly increases the likelihood that the bullet path will traverse an important structure, like a major blood vessel.
Also, if you are able to achieve an extra hit or two with a smaller caliber in the same time as you can achieve fewer hits with a larger one, you greatly increase your chances of scoring an immediately incapacitating shot to the upper CNS, heart, or a great vessel.