For this achievement you need to spend 40 hours in the simulation. All you need to do is load up the game, use a plug and play cable with your controller and let it run over night. No need to rubber band the controller. I used this method to get Switch Hitter and Back in the Day also. After finishing all other achievements I still only had 37 hours on the clock. And as others have stated you need to be in the simulation, not on the ship.
Other players have confirmed that multiple playthroughs will count towards the 40 hours. Just needs to be 40 hours in the simulation.