The fundamental plot lacks reasoning

This is actually a recent theme in movies - the evil insurance adjuster.

For many insurance policies, whether or not to pay out comes down to the subjective decision of an insurance adjuster. There are company guidelines, but in many cases it comes down to what one person thinks.

The plot point usually shows someone who thinks of insurance claims as bits of paper on their desk instead of actual human lives, and we see people being denied cancer treatment, necessary surgeries, etc. From there the plot will either hoist them on their own petard, or exact some form of revenge on them.

On a related note, a coworker once had to evacuate his house before a hurricane rolled ashore. When he got back to his house, the front door had blown open (deadbolt pulled out of the frame) and he basically had a beach in his living room.

He called the insurance company, and the claims agent on the phone was taking notes, etc. When he mentioned the door, she asked, very carefully "Sir, was the door blown open, or was it blown off its hinges? If it was only blown open, that is usually evaluated as resident neglect and not covered. However, if a door is blown off its hinges, that is a structural failure and always covered. So when the adjuster comes out to review the damage, be sure to show him how the door was blown off its hinges in the storm, okay?" and then she hung up.

Of course, when the adjuster arrived, the door was ripped off its hinges and lying in the entryway.

That's the antithesis of what we're talking about here.

Hobbs's wife lost time senselessly because of the insurance writers. Demi Moore's character was consumed with working at the expense of her personal life. Hobbs gave her a life again. At the end Demi Moore gives the female reporter the story so that the reporter can live a more personalbe life as well. Hobbs is the antithesis of the insurance writer and that made a difference. He's hoping to change things for others to make it a better world while deterring the behavior of the insurers.

You equate dental work and cancer?

I could see the idea of wanting revenge on an insurance company.

But he had to wait 15 years before he found an accomplice that he knew was getting fired and would discover this ahead of time?

And then when they install cameras his accomplice manages to find a hole in them that he can exploit?

He may have been very patient but still his plan really depended on a couple of points he had no control over and never knew if they would develop back when his wife died.