> For example, would one say "Captain Picard would have lived many years after Captain Kirk"?
Not for that specific example, but one might certainly speculate "Picard would have retired to his ranch in Marin County after retiring from Starfleet" (I'm guessing the later years of Picard's life have been covered by the fiction, but let's pretend like the series just ended and we're speculating about what the Picard character's later years were like.)
All this having been said, I do think there is supposed to be some ambiguity, or at least some missing information, about what happened to Ingsoc.
Not for that specific example, but one might certainly speculate "Picard would have retired to his ranch in Marin County after retiring from Starfleet" (I'm guessing the later years of Picard's life have been covered by the fiction, but let's pretend like the series just ended and we're speculating about what the Picard character's later years were like.)
All this having been said, I do think there is supposed to be some ambiguity, or at least some missing information, about what happened to Ingsoc.