What’s the catch with this approach

When producing documents you're asserting they're actually real.

So if ChatGPT generates a bunch of stuff that is incriminating, you'll have some 'splaining to do. And potentially contempt of court of the like.

"Restate the following boring document in blandest possible ways, do it 1,000,000 times"

That's still putting a lot of trust into the AI that it's not going to overstep in some way that's problematic to you, and given the lawyers that have to sift through the content you create may not be very happy about it, they might be more than willing to jump on any excuse to cause you problems based on what you submitted.

As an example, just search about ChatGPT being "confidently wrong" or "confidently incorrect". It's also possible that in restating things ChatGPT may be "colloquially accurate" but "legally incorrect" in how it restates things, given it's trained on many sources of natural language, and I think most people would choose to communicate with a court and lawyers (especially ones they assume antagonistic) with a higher level of caution than colloquialisms as they would when speaking informally to others.

I wonder how many times it would take to have decent odds of producing a variant with ‘Amazon is innocent, it’s all a giant frame job I’m doing to them’ or similar in it.

I guess adding some post-processing classifier to check generated docs for self-incrimination would lower the odds by 2-3 magnitudes.

What’s the saying? ‘You can’t build in quality with better QA’?

Haha. You do you, I just can’t imagine any lawyer saying what you’re proposing is a good idea at all.

I mean we need to figure out an admissible way to bankrupt Amazon lawyers like they want to bankrupt us. Tit-for-tat.

Ah, but the key thing you’re missing is that the Amazon lawyers are probably being paid by the hour (at very high rates) and would love to have an excuse to pretend to work for longer.

And you’ll never succeed in bankrupting Amazon.

They could ask the court to block the requests(I presume), if there is demonstrably an excess or errant type of requests, and the court(the judge) will remeber that.

Not clear what the specifics of the order here is, but the catch is he could risk being found in contempt of court or guilty of obstruction of justice depending on the circumstances. A subpoena is a court order compelling either testimony or the production of evidence. If you then go and make up a bunch of new stuff for the purposes of frustrating that court order you could find yourself in some difficulties.

That said, there is such a thing as "malicious compliance" ie complying with an subpoena by supplying the evidence requested in as unhelpful a format as possible. One that I heard of is in a suit related to the Madoff case, Madoff was compelled to produce records of phone calls made from his company and personal phones, so provided thousands of pages of very blurry scanned image pdfs in order to make it difficult for prosecutors (and the trustees, who were working to recover the funds) to OCR them and decipher who he had called. In the end they managed to do this nontheless.

Jail for contempt tends to keep me on the straight and narrow but the again I’m trying to retain my license which may influence my thinking.