One of my TIEs received the stunned pilot crit which causes one damage when I overlap a ship. Now, is it possible to overlap one ship, go back down your flight path, overlap another ship as you are going back, then go down further until you can set your ship. Will this count as 2 overlaps and cause 2 damage?

A ship only over laps another ship if at the end of the maneuvering phase the bases are over lapping, if during flight your maneuvering template or ship base over lap another ship base they are simply flying by each other in space, there is no collision over overlapping, will only result at the end of your maneuvering phase for that ship, can only gain one additional damage per round

or possibly your opponent could crash every one of his ships into yours and purposely give you damage with multiple overlaps, but that would be pretty dickish

Only your final position is relevant to see what you overlap and what not.

Regardless, stunned pilot triggers AFTER your maneuver if you overlapped something during its execution. But it does not cares about how many things you overlapped during it.

Thus, you only suffer one damage.

or possibly your opponent could crash every one of his ships into yours and purposely give you damage with multiple overlaps, but that would be pretty dickish

Jehan beat me to it, but this is wrong enough to deserve another countervoice.

Stunned Pilot only does damage when you overlap something; not when something overlaps you. Your opponent could pile his entire squadron on top of your Stunned Pilot and you'd be just fine.

What about a ship that ends its manuever overlapping an asteroid and a ship? is that 1 damage for each overlap as well as a roll for the maneuver through the rock?

If you are under 'stunned pilot' critical hit and your movement ends overlapping a ship, you take one damage. If after resolving the overlap, your ship or your template also ends overlapping an obstacle, you would roll a red die and take damage according to the roll.

However, note that when resolving the ship's overlap and backtracking your movement, your final position may end before reaching the obstacle. In this particular case, you do not suffer any ill consecuences from the obstacle, even if your template originally overlapped it.

Why would you roll for overlapping the obstacle? Stunned pilot says take damage for overlapping ships or obstacles. it would seem to me you would roll the red die as per normal plus take one damage for overlapping a ship plus take another damage for overlapping the obstacle.

Why would you roll for overlapping the obstacle? Stunned pilot says take damage for overlapping ships or obstacles. it would seem to me you would roll the red die as per normal plus take one damage for overlapping a ship plus take another damage for overlapping the obstacle.

Note that the card says 'EITHER another ship or obstacle'.

You don't suffer extra damage even if you overlap several obstacles, or ships. the same way as you don't roll a die for each asteroid your template overlaps. It is just 1 single damage for overlapping something, not 1 damage for each different thing you overlap.

The trigger only happens once. 'After you execute a maneuver'. If the condition is met (you overlapped either a ship or obstacle) you suffer one damage. Additional overlaps have no effect on the critical card.

ok that makes sense if you are overlapping a ship and asteroid that you dont take two damage. but it would still seem you rool the die for moving through the rock as usual then take the extra crit damage if you land on it or a ship.