I make it a preference to take any coon I seen on or near my property. A few years back we had a rabies epidemic ranging up the east coast from Washington D.C., to Montreal. Most of the critters affected were the racoons, although we had some whitetail and a few others infected. All in all I believe I have taken probalby two dozen racoons in the past 10 years.
On most occasions I would use a 22lr from either a AR-7 or a 10/22, but a few times I used a 22lr pistol, or a 45 auto, depending on what I had when I encountered them. I knew from experience they were tough critters and also knew that I didn't want a lot of rabies infected blood laying around after they were shot, so I would shoot for the head. That would only take one shot, most of the time, with standard velocity 22lrs and solid nosed slugs. With the 45 I would go for a head shot and there was no contest at all, they were dead before they fell from the tree. I saw the same effect with head shots from the 22 pistol or either of the 22 rifles if I aimed for, and hit the head. In one situation I helped a neighbor clean a racoon colony out of a barn he was rehabing, and most of the kills were 1 shot with a 22 lr to the brainpan.
One fellow I knew was a crooked rehaber - he wa supposed to take the animals to another distant location and reloacte them but we found he was simply trapping them and killing them for their pelts. When I encountered him he was dispatching caged animals with s 22 shot to the head and fortunately he was good enough to make it a quick one shot kill, although just about as unethical as I have seen.
I also know from experience that racoons carry a virus on their teeth that will permanently diasable and blind a dog if the dog is bitten, so I try and keep my dogs away from them. Although my guys are vaccinated against rabies I still don't want to chance a torn face/muzzle or a permanent injury to my pets.
Racoons, like any wild animal, don't go down hollywood style, they will try and run or fight if they have to. In thinking about dealing with just racoons, I feel the 22 magnum is a better choice than the 22lr, a 38 wadcutter would be very effective, any big bore with a slow moving flat nosed slug, or now possibly one of the 17 calibers, the new necked down 22 mags or 22lr. HTH. Mikey.