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I highly doubt she knows how his wife is, and I don't think we are expected to believe she knows. I think the point of her saying that was to calm Jack down and we are to take nothing more than that away from it.
I'll agree with that.

However, the episode showed that the Others had/have very significant contact with the world (Stephen King novel?). So who knows what they can know.

Of course, this was the first episode I've ever watched.
The novel was Carrie, which was first published in 1974, so that doesn't really prove much, that's 30 years before the plane crash.

Of more interest is that "Downtown" was played on a CD - I've not yet verified when it was first printed onto CD, because it is a bitch to search through all Clark's compilation CDs, but it might narrow down a date of The Other's definite last contact with the outside world.
My best guess would be '86. That's when Petula Clark's Greatest Hits CD was released. The studio album that Downtown was on wasn't released until 1994 in CD form.