I drew the stunned pilot card this week. It states that when you run into a ship or obstacle you take one face down damage. My question is does this card count as one damage when drawn, then a second when you run into something, with the possibility of gaining a third damage if you run into an asteroid?

Thank you in advance for the clarification!

Yes, the crit card counts as a damage, they all do. The card reads "After you execute a maneuver that causes you to overlap either another ship or obstacle token, suffer 1 damage." This means anytime your ship ends its movement on top of a ship or obstacle, you take 1 damage, which (if you haven't regenerated a shield with R2D2 or Chewie) means you draw another damage card.