I am looking to fly him and just what to double check when his ability activates.

1. As soon as he loses a shield (what i think)
2. As soon as he losses a hull

2 - a ship is damaged while it has at least one damage card.

Dealing damage to a ship, does not make it damaged. (and I think this is where your confusion is from.)

"A ship is damaged while it has at least one damage card. A ship is
critically damaged while it has at least one faceup damage card." - page 8 of the rules reference.

So he is not damaged until a card is on him.

Ok thanks so a hull upgrade is better and cheaper.

1 hour ago, player3049613 said:

Ok thanks so a hull upgrade is better and cheaper.

I guess on Wullforo it might actually be... cool.