So, I've been wondering about this for a while and a few days ago it actually happened! I flew a ship through 2 obstacles, a rock and debris. Now, when firing, you only country obstructions once, regardless of how many obstacles you are shooting through. So when flying, do I only react to one or both? And if only one, which one? For the game, I stressed myself for the debris and rolled for both (no dmg at all much to my opponents dismay heehee) but I'd like an official ruling for the future

From the Rules Reference page 14.

If a ship moves through or overlaps more than one obstacle, it suffers the effects of each obstacle, starting with the obstacle that was closest to the ship in its starting position and proceeding outward.

Edit, ninja'd

From the Rules Reference page 14.

If a ship moves through or overlaps more than one obstacle, it suffers the effects of each obstacle, starting with the obstacle that was closest to the ship in its starting position and proceeding outward.

That is the current ruling.

Back before the Debris became legal obstacles I believe you only counted/rolled for things once. If you hit two rocks it was no worse than hitting just one. Now when it comes to firing a shot is either obstructed or not but when Debris hit the scene the chance to run over two different things became a possibly which is why you now count everything you hit.

I gotta say,I only country too!