When you meet the mechanics for the first time at the Temple, ask them who they are.
When in the Blue Casket during Year 2, do the following:
Stand in front of Eva's desk to find her hole puncher. Interact with it and Manny will ask if he can use. Eva will allow it. Do not hold any of the cards that you can find in the first room where the game started.
When inside the Temple where you earn "Happy trails, Captain", move to the tunnel that Chepito entered. Manny will stop there and "I could walk out out of this world and not look back..." will be earned.
In Rubacava during Year 1, go to the dock where Velasco is located. You can find a skull-faced moon at the top left. Select the "Look" button at it.
Talk to Glottis the car mechanic. Exhaust all the dialogue options until only "You want to be my replacement driver?" and "Alright, back in the shack, mac" are the choices. Tell him to go back into the shack. This must be done before you ask him to become your replacement driver.
Note: This is can be missed. Do the following before you get Eva to sign. When outside of the Department of Deaths building, turn right outside of the entrance. Pass the alley and go to the location with a colorful floating donkey. Speak with the balloon-practicing clown in front of the tents to the right. He is upset. Make him create balloon sculptures for you. Talk to him until the "Bang" option appears, then select it to scare him into popping one of his balloons.
Progress until reaching Rubacava during second year. Just before the end of the chapter and after freeing Terry from jail, go where the bees are striking. Sing with them and try to be in time. You must sing after Terry, in time with the other bees. After completing the entire sing, they will cheer you on. Cto sing with them until "ME, ME, ME-ME-ME!" is earned.
When you find the Rusty Anchor letter from Lola's coat, show it to Glottis. He will then play the song for you. Note: If you have showed Glottis the VIP card earlier, he will be at the High Roller Lounge instead of the cafe, and you will no longer be able to earn "Oh Rusty Anchor".
When you return to Rubacava, go to the lighthouse.