Some points about boarding party..
1. I thought so too that chest wouldn't open after you wipe/reset on it once but a guildie told me they got the chest to open sometimes even after a couple wipes so I am not even sure anymore..
2. The kill order that worked for us was Medic --> Commander --> Massey (Chief in your version). Massey hits pretty hard but can be kited. Our tank grabbed Commander and Massey and kited them away from the rest of group which focused on the medic. After the medic died, we kill Commander Jorland. Shortly after this, the encounter will enrage and you can just kite Massey around while the ranged dps kill him.
Leaving the chief at the end is also a good option if your dps isn't very high, and your healer is able to keep up until the commander dies. However, it creates a very messy fight. At least with the healer as the last target, you guarantee the enraged mob on the tank, who should be spreading out his cooldowns to buy a lot of time.
Nonetheless, it is a good option for low dps groups.
About the loot chests, the only explanation I can come up with, is that your friend got lucky with the chest. I guess there is a small chance that the chest will not bug even after a couple of wipes. It is a little odd, but about 95% of the time, it will bug if you wipe.