On the other hand, Bos and NY would have had two chances to win a game and get into the playoffs; Cleveland would have only had one all-or-nothing game.
Yes, of course that’s correct. My mistake. As Skammer points out this is actually advantageous for New york and Boston, and disadvantageous for Cleveland. Which to be honest is fair, since New York and Boston finished atop their division and Cleveland, even in this hypothetical, did not; in effect they would already have lost their contest with Chicago for the Central title and so don’t deserve two shots at the playoffs.
I was confusing this situation with the other three-team playoff situation. Suppose that New York had finished clearly ahead of Boston, and that Boston, Cleveland and Oakland had all finished 94-68 and tied for the wild card. In THAT circumstance, two teams get screwed; they have to play off against each other and then play the third team for the wild card. This would also apply if three teams tied for a division title but the wild card came from another division.