I appreciate the advice that is coming my way.
While the property is rural, it is built up on 3 sides with about 20 homes. While I had been given permission to deer hunt there a few years back, even though I would be using a shotgun, I would have extreme reservations hunting on the property with the horses kept in their stalls.
I just did a quick search on an auction site, I have learned that most of the listed, used Model 10s and 64s are listing for more than an M&P Shield! I do like the appeal of a shotgun, but the thug is riding "2 up" with his stepson, who may be a "tween", but would most likely be in the line of fire.
If there were a safe place to shoot, I would not be against allowing them to try some of my more appropriate handguns (a 36-6, a 686+, and a G17). The problem is, most of my hardware is designed for target shooting, with longer barrels and 3Ts. The big problem seems to be that this thug has no respect for anyone, anyone else's property, or authority. Definitely a bad combination that doesn't suggest a reasonable resolution.
Sounds to me like arming up with the expectation of a confrontation is premature, especially with a general lack of experience and the likelihood of others being within the threat area. I have no problems with individuals preparing and acting in defense of themselves, their families, their homes, and their properties, but the situation described is setting off alarm bells in my head.
An apparently notorious bad actor, usually accompanied by an underage juvenile, repeatedly trespassing and engaging in aggressive behavior against the lawful property owners. The circumstances almost shout "CAUTION" in my ears, not just physical caution but great care not to create civil or criminal complaints that could be devastating in scope. Believe it or not, but there are more than a few lawyers out there who would jump on the bandwagon for lawsuits against a property owner who engaged in (lawyers' words) negligent, malicious, or violent means against their poor client who was just out enjoying the day on his ATV and may have inadvertently crossed a property line with no intent to trespass, etc, etc, etc, fill in the blanks (just like lawyers do in court pleadings).
Step 1: Document, document, document. Every telephone call to law enforcement, every complaint made, logged by date, time, officers' names, full details. Trail cameras or video recordings if at all possible, copies to authorities. Perhaps a letter from the property owner's attorney demanding compliance with trespass laws, a copy of the recorded legal boundaries of the property by public records, couple of pages of lawyer mumbo jumbo thrown in for effect.
Step 2: Establish a pattern if possible. Mornings, evenings, weekends, weekdays, whatever; there is usually a pattern to peoples' behaviors.
Step 3: Request law enforcement action based on the information documented. Patrols, surveillance, static assignment on days and times when these incidents are most likely to occur. Cops are more likely to commit resources when the commitment is likely to result in successful intervention.
Step 4: Assuming no LE responsiveness, consider retaining a licensed private security company to intervene on specific days and times when violations are most likely. Such companies are licensed, bonded, and insured so the risks to the property owner are much less than direct personal intervention (armed or otherwise). Consult an attorney regarding a certificate naming the property owner as an additional insured on the security company's liability policy for the duration of the contract.
Signs (NO TRESPASSING, KEEP OUT RIFLE RANGE IN USE, whatever) are fine, but not an absolute protection against civil claims. Covered pits (full of pig poop or whatever) or tire flattening devices might be effective but might also lead to escalating confrontation.
Everything I am hearing from the OP says this is a seriously bad actor who has decided (for whatever reasons) that he is going to impose his will on the property owner and continue a campaign of terror. That guy needs to learn that the only possible conclusion involves handcuffs and criminal charges.
Assuming that is the end result, THEN the property owner will need to have effective means of self-defense in the event that Mr. Bozo decides to retaliate. Much easier to explain to a jury why reasonably necessary force was required when Mr. Bozo comes back to continue the contest after being introduced to the proper mechanisms of legal proceedings.