I'm no tax lawer, but in my view, if it is appropriate for pilot 1 then the question is really about pilot 2's employment status.
If he has resigned, left and had his holiday's paid out then he is effectively in the same position as pilot 1. However if he is taking leave and his resignation is effective at the end of his leave then he is not in the same position.
If his previous employer is nice, they'd make his resignation efficient on same date as pilot 1 and simply show his leave as a termination entitlement.
Good luck.