I have hunted boar quite a few times with a handgun in Lake Wales, Florida. I used a .44 magnum.
The first boar I hunted had to be shot 3 times. And, he chased us twice. Boar only run straight, so hard lefts and rights shook him off. I found that the reason for needing 3 shots was because I was using 240 grain Remington SP ammo. The SP bullets (and HPs) do not penetrate enough to drop a 250 pound boar. Their shoulder armor can be more than an inch and a half thick.
My next time out, I was loaded with my own hand-loads: 240 grain flat-nosed full copper jacketed bullets over a hot load of 2400. I dropped a 200+lb. boar with one shot to the right front shoulder. When we quartered the boar, we found the spent bullet in the left rear thigh. After that, I only used solid bullets.
So, I would strongly suggest that you not use hollow points, and .44mag is as small as I'll go with a handgun. A week earlier, a guy grazed a big boar and it charged him. He tried to run, but fell down. He ended up with 125 stitches up the inside of his thigh..... very close to his prized jewels.
As for what to do with the boar after you shoot it.... it's the best tasting pork you'll ever eat.
