alt Hacker NewsCourts have already set a precedent on this (it's fair use) and even if these decisions were overturned, the liability would fall on the LLM creators for the initial training, not on their users. The outputs would keep being treated individually on their own merits.
Not really, no. There have been many settlements of lawsuits, which means they are very explicitly not precedents. The LLM companies likely prefer to settle because of the existential risk being found liable for copyright infringement would result in, whereas even an expensive settlement doesn’t upend their entire business model.
Furthermore, I don’t think you can really assume that the courts will rule a certain way on this just because of the money involved; there’s a lot of money involved when it comes to the copyright holders too, and they’ve long enjoyed a rather favorable status with the courts and legislators. (For example, in the days of P2P file sharing lawsuits and attempts to legislate P2P file sharing, the software industry was already many times the size of the media industry, but the media industry consistently won.)