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I think if someone is actually cut and brought back it should count but yeah as someone else said, R-Truth was never out of contract so I agree he shouldn't count
First of all Sky can run the game however she likes. I feel that this is fair, given that the OP does state that the winner will be the player who has the fewest wrestlers still in WWE. It says nothing about most released performers. In this instance R-Truth never left the company, but even if he did he is (if he makes it to Mania) he is still in WWE so no points awarded.
At the end, the winner will be the player who has the fewest wrestlers still in WWE, and will receive a meaningless prize (a low-quality sig banner created by yours truly).