We'll Sit Down and Have a Talk
Complete the main game.
First thing you will want to do is just play the “main game.” Pick whatever dialogue choices you want to and just enjoy the story.

Until Next Time
Complete the epilogue.
Next thing you will want to do is to choose to “continue to epilogue” after beating the main game. Choose to [call mom], and specifically tell her that your bus is 404 and disagree with her advice that you should get on just any bus. Make sure to stay positive throughout the conversation and diffuse any brief arguments. In my playthrough I chose to continually walk to the right during the conversation (similar to the main game)… eventually I reached a new bus stop and my bus (404) was there, so the conversation ended and I got on and earned the achievement.

Update: According to the developers, the trick to steering this conversation in the correct direction is to be sure to talk about all three things when your mom asks (something along the lines of) “is there anything else bothering you…”

Canon
Don't call mom.
Start the epilogue again from the main menu, but this time choose to [just wait] instead of [call mom]. Get on the first bus that appears. Easy.

Wrong Bus
Get on the wrong bus.
Start the epilogue for the third time, choose “a whole lot” of snow. (Probably doesn’t matter, but it’s what I chose). This time [call mom] again. Tell her your bus is the 404 but this time agree with her that it doesn’t really matter if you just get on a different one. Now stay at the bus stop and try to be as argumentative as possible with your mom. After a short amount of talking, a bus that isn’t the right one will arrive and your mom will tell you to just get on it and hang up.

Update: Be dismissive of the conversation when your mom asks (something along the lines of) “is there anything else bothering you…”

70 out of 100
View all of Kelly's photographs.
From the “more” menu, view the photographs and be sure to scroll through all of them before exiting.

By Benji
Read all of Ben's stories.
From the “more” menu, view each of Benji’s stories and be sure to scroll through all of them before exiting.

On the Radio
Listen to all songs on the radio.
From the “more” menu, start up the radio and you must let every song play from start to finish. (annoying… probably best to do while doing something else). (If you find an easier way to do this, please feel free to post a comment).

Home
Complete the main game, epilogue, and all extras.
With everything else done, start up the epilogue one final time, and choose [just wait] and then get on the first bus. (Like you did for Canon). After the credits, you will be shown a brief bonus scene and then this final achievement will pop.

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