However, it's worth noting the universe is a cesspool of corruption. If you pretend it works the way it ought to and not the way it does, you won't have a very good time or be very successful. The entire legal system is f-ed, and if you pretend it's anything else, you'll end up in prison or worse.
Why would the judge have to assume anything? The person suing could simply tell the judge they did mean to use the older interpretation, and that they disagree with the "fix". They're the ones that get to decide, since they agreed to post content using that specific license, not the "fixed" one.
A court would probably not agree on the fact that writing "IANAL", not the full sentence, is a sufficient disclaimer.
You see this particularly with crypto, where "I am not a crypto expert" is usually accompanied by a more factual statement than one from the self proclaimed expert elsewhere in the thread.
I always assumed it was the same type of courtesy as IMHO, and someone taking legal advice from random strangers on the internet wouldn't result in any legal liability on the side of the commenters.
I remember hearing about an construction engineer who was sued for giving bad advice whilst drunk to a farmer over fixing a dam. The dam failed and the engineer was found to be liable.
When it comes to lawyers, there is already a legal framework where lawyers are responsible when giving legal advice, even when it's not toward their clients, the same way medical professionals have specific liabilities regarding the medical acts they can perfom.
Non lawyers giving legal advice doesn't fit that framing, except if they explicitely pose as one. I'd also exclude malicious intent, as whatever the circumstances, if it can be proven and results in actual harm there's probably no escape for the perpetrator.
One cannot legally practice law without a license. The definition of that varies by jurisdiction. Fortunately, in my jurisdiction, "practicing law" generally implies taking money, and it's very hard to get in trouble for practicing law without a license. However, my jurisdiction is a bit of an outlier here. Yours might differ.
In general, the line is drawn at the difference between providing legal information and legal advice.
Generic legal discussions, like this one, are generally not considered practicing law. Legal information is also okay. If I say "the definition of manslaughter is ...," or "USC ___ says ___," I'm generally in the clear.
Where the line is crossed is in interpreting law for a specific context. If I say "You committed manslaughter and not murder because of ____, which implies ____," or "You'd be breaking contract ____ because clause 5 says ____, and what you're doing is ____," that's legal advice.
The reasons cited for this are multifold, but include non-obvious ones, such as that clients will generally present their case from their perspective. A non-lawyer will be unlikely to have experience with what questions to ask to get a more objective view (or even if the client is objective, what information they might need to make a determination). Even if you are an expert in the law, it's very easy to accidentally give incorrect advice, which can have severe consequences.
In practice, most of this is protectionism. Bar associations act like a guild. Lawyers are mostly incompetent crooks, and most are not very qualified to provide legal advice either, but c'est la vie. If you've worked with corporate lawyers, this statement might come off as misguided, but the vast majority of lawyers are two-bit operations handling hit-and-runs, divorces, and similar.
In either case, it's helpful to give the disclaimer so you know I'm not a lawyer, and don't rely on anything I say. It's fine for casual conversation, but if tomorrow you want to start a startup which helps people with legal problems, talk to a qualified lawyer, and don't rely on a random internet post like this one.
Which does exist and can affect the ruling. CC notably didn't grant sui generis database rights until 4.0, and I'm aware of at least one case where this could have mattered in South Korea because the plaintiff argued that these rights were never granted to and thus violated by the defendant. Ultimately it was found that the plaintiff didn't have database rights anyway, but could have been else.
Programmers think like machines. Lawyers don't. A lot of confusion comes from this. To be clear, there are places where law is machine-like, but I believe licensing is not one of them.
If two licenses are substantively equivalent, a court is likely to rule that it's a-okay. One would most likely need to show a substantive difference to have a case.
IANAL, but this is based on one conversation with a law professor specializing in this stuff, so it's also not completely uninformed. But it matches up with what you wrote. If your history is right, the 2019 changes is where there would be a case.
The joyful part here is that there are 200 countries in the world, and in many, the 3.0->4.0 would be a valid complaint. I suspect this would not fly in most common law jurisdictions (British Empire), but it would be fine in many statutory law ones (e.g. France). In the internet age, you can be sued anywhere!