Could this land him in court?
Anything that upsets another person can land someone in court. It has nothing to do with whether they are in the right, legal or not.
Just about anyone can sue over most things. It just has to be presented a certain way by a competent attorney that presents it as close to applicable law as possible for that location.
For example I have seen people completely make up false things, sue over them, and while not winning cost the sued person tens of thousands of dollars fighting a case over a year or two.
So the fact that the other fabricated things out of thin air to be spiteful to a disliked neighbor did not relieve them of the cost to defend themselves in court.
Multiple motions to extend and delay filed by the suing party, who had no factual case, resulted in the other attorney needing to match each filed motion with additional paperwork. Each time charging for many hours of work.
Since they knew they couldn't actually win they just filed for numerous delays and various motions to cause the sued party a lot of legal costs. Then they dropped thier case when they saw they could not outspend the person they sued.
Keeping a counter suit alive to try to reclaim some of those lost funds would have required tens of thousands more, and it would have been an uphill battle for them to show the lawsuit was only for malicious punishment and not at least believed by the other party.
If someone was crooked and did not like the T-shirt you wear around the neighborhood they could think of some random or exaggerated thing to sue you for. Perhaps claim they walk across your yard and have been for years, and sue for an easement (does not have to be true or have any basis in reality.).
Then they can spend tens of thousands, and require you to spend similar amounts to counter every filed motion with legal paperwork from your own lawyer.
Someone can extend, postpone, dismiss, re-file, and file dozens of similar motions without ever actually getting to the real facts and details of the case or a conclusion.
If they know they can last longer than you can, then they can destroy you even without a case as long as they are willing to lose around as much money as they want thier victim to lose.
Something a retired person with a fixed or limited income should consider.
Of course a retired 80+ year old man losing all he has without many years left of life may also pose a threat to such a dishonest person and not care so much about the consequences.
So both sides should consider potential consequences of actions.
So yes something that upsets another person can always land you in court, legal or not. But being a pushover also means others will just walk over top of you and your rights.
So it is for each man to choose his own battles, because the consequences of each decision will effect them more than anyone else.