As Dusk Falls

For some reason I couldn't get the guides already on here to work for me, but this game does seem to genuinely alter based on various choices, so this is the combo that worked for me.
This takes place in Chapter 1, if you're replaying from 'explore story' you can pick the scene "Big Sam Arrives" and start from there.

Earlier in the episode I had lied and said it was just Me & Dad to the robbers. So the wife and kid were safe until they came into the room during this scene. I'm not sure if this will work if your family has already been found.
Choices in this order;

Don't Move Evidence

Wife and Kid

On the Run

Fugitives on The Loose

Help

If Big Sam tells you that he will call for backup and "you should laugh like (he) just told you a joke" then you did this correctly.

To earn this achievement you need Big Sam to become suspicious of Vince and his wellbeing without raising the Holt's suspicions.

To accomplish this, load up the "Holts Stormed the Motel" section of the Chapter 1 story tree.

The important decisions which will impact this achievement are as follows:

When asked by the Holts who you're with, choose "Just my dad".
When Big Sam enters and Vince looks at the earring on the ground, choose to hide the evidence.
When asked by Big Sam who you're with, once again choose "Just my dad".
When your wife enters the motel, wait for a few moments after the two dialogue options appear. A third option will appear above the first two saying "Nothing", select this.
When Big Sam and your wife ask if everything is okay, just say "Yep".

Big Sam will walk past you as he leaves and let you know he's going to call for back up. Your achievement should then pop.

This can be found in the video below at the 4:28 mark.

This is during the scene where the three Brothers have everyone hostage at the motel and the cop comes in and starts asking questions.

The answers I gave were:

•don’t hide evidence (Blue earring)

•Help

Tell Tyler Vince is only with his dad.
Hide evidence.
Tell Sam that Vince is only whit his dad.
Tell Michelle Nothing.

For a Full and Fast Achievements Guide check the link below:


Timestamps:

00:00 Intro + Useful Information
02:02 Chapter 1: Story
03:49 Chapter 1: Code Breaker + Smooth Criminal Achievements
05:14 Chapter 1: Message Received + Tables Turned + And So It Begins… Achievements
06:32 Chapter 1: Bungled Achievement
07:16 Chapter 1: Cop Out + Point Blank Achievements
08:18 Chapter 2: What’s Your Emergency? Achievement
09:12 Chapter 2: Story
10:08 Chapter 2: Paging Dr. Walker Achievement
10:57 Chapter 2: Keeping The Faith + Second Chance + Lifesaver Achievements
11:56 Chapter 2: Dodged A Bullet + Caught in a Trap Achievements
12:21 Chapter 2: What’s Done is Done + Unforgiveable Achievements
13:32 Chapter 3: Long Arm of the Law
14:01 Chapter 3: Story
14:24 Chapter 3: Resurrection Achievement
14:48 Chapter 3: Take Me Instead + New Dawn + From Dusk ‘til Dawn Achievements
15:59 Chapter 3: Better the Devil You Know Achievement
16:23 Chapter 3: Buried Alive Achievement
16:44 Chapter 3: She’s Coming with Us Achievement
17:18 Chapter 4: Invincible Achievement
17:49 Chapter 4: Story
18:46 Chapter 4: Cabin? What Cabin? + Brothers in Arms + Into The Woods Achievements
19:46 Chapter 4: Trail of Breadcrumbs + Once a Holt + Hands in the Air + No Going Back Achievement
21:19 Chapter 5: Bullseye Achievement
22:04 Chapter 5: Plead the 5th Achievement
22:28 Chapter 5: Story
22:54 Chapter 5: Jailbird Achievement
23:23 Chapter 5: Heart to Heart + Bonnie and Clyde + Runaways Achievements
24:14 Chapter 5: Cuba Libre Achievement
24:58 Chapter 6: Story (Wait for the Cop)
25:43 Chapter 6: Into the Wild + Breaking Bread + Past, Tense + End of the Road? Achievements
26:56 Chapter 6: Almost Made It + Enough is Enough + Stay of Execution
27:47 Chapter 6: You’re On Your Own (Chapter5) + Free Bird + Most Wanted Achievements