Updated 02-03-2024 03:39 PM
Disclaimer: Complete "Playing Doctor Achievement" before starting any missions at the beginning of the game in Portland. It will become extremely difficult once gang members become hostile.
Missable: Triads and Tribulations mission: You can save the game if you want, it’s quite easy to unlock this achievement.
You will have 2 gangsters with you and they need to stay alive. You need to kill 3 groups of enemies but there are many rival gangs on the streets. I would suggest using your vehicle to kill the closest enemy.
1: Go to the closest enemies first. Run them over
2: Go to the farthest enemies next. Go around the back of the warehouse area and up a grassy hill. You can shoot at them from the hill.
3: Lastly, go to the enemies in the alley, these are quite difficult as your vehicle can’t get through the bollards. I stopped near the bollards and charged at the rival gang. If one of the gangsters dies before this point, restart the mission by letting a rival gang member kill you.
You will unlock the achievement if both of your gangsters are still alive. I recommend doing the alley one last as it’s quite difficult to get back in the vehicle without your allies getting killed.