I no longer work for IELLO.
Let's say I don't have any pirate cards in my crew. You play your cards in the order of your choice, so in your example, the sensible way would be to play the Beer first so the Pirate is safe.
I draw a share which consists of the Beer card and a Pirate card. The Beer card requires that I discard a Pirate card. Do I have to discard the Pirate card that I drew with the Beer card, or is it safe because it is not a part of my loot yet?