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This is a scrimmage kick and not a free kick. Also there is no rule against entering the field just before the snap. This isn't Canada, if they can get on and get set then let them do it.
In both situations it is, by the book, illegal formation under 7-2-1. 7-2-1 has no get-out-of-jail-free provision based on if the defense covers the player.
However some officials might say that in situation A, and possibly B (but that is a harder case to prove), there was also intent to deceive the defense into thinking this player was not in the game and have illegal participation under 9-6-4d. This might be a case where a wing has the foul for illegal formation and then the kickers throw the ball to the player who came on late because he was uncovered. In this situation the call might change from IF to IP whereas if they just punt the ball then it would probably stay as IF.
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