You mention dogs being a legal liability. Talk about liability issues? Own an unvaccinated racoon and have it bite someone.
That and within city limits in urban areas like NYC there are lot things that are a legal liabilities and as a result not very popular.
Back to racoons. I have never owned sheep so I am not qualified to opine on the subject of herding them.
That said I do own 4 legged live stock as well as apparently by default, a bunch of raccoons (opossums & feral pigs)that live in the nearby area on my acreage. My live stock associate me with food and treats so I am frequently followed by a menagerie seeking more treats. They rarely need to be herded. YMMV.
BTW the legal liability is less so a problem when you own a farm and they are considered working animals. In LA, TX,AL, & MS (the states I know) there is a specific legal liability protection for issues dealing with animals on in an agricultural setting so long as the animal stays on the owners property. Trespassing is highly frowned upon in the agricultural world for the same reason us poor simple country folk knew years ago to use PPE, wash our hands and disinfect our boots frequently.
https://www.mysafetysign.com/louisiana- ... k2-1863-la
As to specifically keeping a racoon as either a pet or working animal there are 2 key issues with that.
In some (not all states) it is illegal for anyone but a certified (in that state) wildlife rehabilitator to keep wild animals. If no such resources is available the DWF typically seizes and the destroys the wild animal. So first you have to pass that hurdle either by certification or legality.
The bigger issue is health care for a racoon. Many vets will not touch them. The few that do will charge a premium. There are only 2 rabies vaccines approved for their use. They are oral and expensive. The other issue is distemper which is actually a broader health issue than rabies. Racoons can contract both canine and feline distemper. I am not aware of a vaccine for distemper in racoons (there may be but that is outside of field of expertise). BTW the vast majority of sick racoons that you will see are not rabid but rather have distemper. It is fatal to them and they can transmit the disease to unvaccinated animals.
If you raise any animals that can contract distemper & rabies (which basically is any mammal) you want to very careful about the potential for disease and parasites. You also want your working animals to be able to receive medical care from a close by vet. That or if you pay for a house call which is common you may as well get all the animals in need of care addressed.
My take on racoons is that they are welcome on my property up until they predate upon any of my animals. They are dealt with at that time. They do come and eat the barn cat's food but the cats seem to tolerate this up to a point. My wife did lose a batch of chicks to these racoons when they ate some but not all of the parts of the chicks leaving the the group dead, dying and dismembered. The next night a relocation notice was served upon those racoons who returned.
IMO opossums and racoons (but not f'ing feral pigs!) are needed in a limited quantity but they will all hunt and kill a disproportionate number of wild turkey chicks as well and any other baby animal (including but not limited to kittens, chicks, fawns) they can find. I would note that my live and let live policy that I follow is not supported by studies that suggest a more vigorous population control is recommended. YMMV
https://digitalcommons.unl.edu/cgi/view ... ey+nest%22
As for the comic book cartoons; I have never seen a racoon drive or use a weapon. That is why it is called fantasy fiction.