I knew a chap who left where I used to work to go to a large UK bank at high end contracting rates.
He returned after a few months saying that the team he joined (which was apparently quite large) had been given no work in that time and hadn't even been given any computers - and they weren't allowed to use their own devices for anything. He said he left simply because he couldn't take the boredom - even though, as he freely admitted, the money was fantastic.
Going along with the original story, I could go either way on this. On the one hand, paying someone $40k to do it, probably involves more supervision and turnover, and a chance of someone making a mistake. And then you get to tell your million dollar client: "We lost our case because our semi-skilled clerk misplaced a file and we have no IT department."
On the other hand, what would you pay an outside developer to automate the process and guarantee accuracy, maintenance, and uptime? Could you even do this with no GUI, no dashboard, no management fanfare, and no brainstorming of unnecessary features?
Yeah this is the big red flag for me. I believe that a law firm without a ton of technical knowledge would hire someone to do this work manually, but they'd get an intern or something, this is not skilled work.
It's easy to overstate the technical difficulty of lots of basic IT work, especially if people are tech illiterate.
There might be an element of deliberate fraud if this guy is spelling out the difficulty of the job as justifying his pay to management. I've seen very clever goldbricking similar to this, where management doesn't know enough to understand what good IT looks like, or how to value IT work.
On the other side: the business can clearly afford it, so the value he brings is entirely justified from a commercial perspective. The fact that they can find cheaper alternatives on the IT market is a different issue.
You can buy a new branded car for $$$ and be sure it will work for years with minimal maintenance, or you can shop around and buy a passable 15-year-old car; in both cases it will likely get you from A to B for a while, but the chance of having problems is lower with the new "whip". This guy, to the business, is the equivalent of leasing a new car every year: they can afford it and brings no risk as far as they can see.
The obsession with capital efficiency can often turn into a disease. Why should we drive down our own wages, when the market is willing to pay more?
This is basically why I do not automatically discount the story as fake. I have certainly been a part of groups that had a wide range of technical skills. It is an odd experience, but it forces you to think about your audience ( and document everything like you would for your parent ).
I do have an anecdote in a similar vein from a buddy, but he does sometimes tend to exaggerate sometimes so I won't mention it. I absolutely believe though there are companies are still run in a very traditional way for one reason or another.