So how do the courts typically resolve the equivocation that the plaintiff has historically and routinely taken advantage of, even as part of this lawsuit?

The root issue is that he created a program whose name happened to be EMAIL so when laymen misinterpret the claim to mean "e-mail" and the plaintiff doesn't correct them, it results in confusion that benefits him. The reporter tried to cast light on that and it seems like the plaintiff is trying to leverage the same confusion to win in court.