I do think Cooper intended to jump shortly after takeoff. Can you imagine his anxiety as that opportunity quickly passed? Everything was changing and his control of the situation was vanishing.
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You seem to forget what is holding this hijacking together - its the threat of a bomb in closed quarters. If C bails early in a more urban environment not only is the risk higher he can be surrounded, but his bomb is neutralised and offers no protection. His bomb is central to the whole plan... and dictates when and where he will bail.
His personal protection relies on the bomb and clearing the plane of people. Only then is he free to conduct his escape without interference. The further he gets away from an urban area, the better. He does not promise he will even take the bomb with him. This creates the idea that he has left the plane but his bomb is still active on the plane. This keeps people from even going to the back to look! Meanwhile Cooper is gone/has bailed. None of that can happen if he bails early ... and Cooper knows it.
The 'tell' I focus on is Cooper's psychology. It is key to his plan and his thinking process. His bomb is a fundamental element in his plan. His choice of Tina versus Flo or Hancock is another critical 'tell'. Nyrop has guaranteed cooperation. Why change what has become a working strategy? Bailing early changes what is coming together as a working plan! Why change a working scenario? He wont and he doesn't, by choice. He's a smart guy who stays with what is working . . . bailing early would only change the whole dynamic. Cooper cannot afford to change what has come together.
What Cooper did and did not do - his choices - tells us a lot about Cooper's thinking process. Bailing early was never part of his plan. There is nothing that favours him doing that, and much that favours him not doing that! Cooper boarded the plane with the skeleton of a plan. When things came together he chose to stick with what was working ... he had no rigid plan to bail early. He worked the situation as it developed...