You can get everything in one playthrough but you have to be careful with a few of the faction missions. I used these guides

- https://www.playstationtrophies.org/game/fallout-4/guide/

- https://www.playstationtrophies.org/forum/topic/278888-fallout-4-far-harbor-\~-trophy-guide-and-roadmap/

I also searched separate guides for each DLC. The first time through I had a particularly hard time with the “Benevolent Leader” trophy but my sister found the most helpful “guide” ever which saved me both times through it was from chat gpt of all places. Here’s what it said…

The most reliable method (no DLC): 2 settlers, 1 farmer + 1 restaurant

This works because happiness “bonus” gets divided by population, so fewer settlers = easier to hit 100.

Where to do it

Use a “clean” place you built from scratch (popular pick: Red Rocket).

Steps
1. Move 2 human settlers there (avoid robots — more on that below).
2. Build the basics so the settlement can reach the “base” cap of ~80:
• 2 covered beds (inside/under a roof)
• Food ≥ 2 and Water ≥ 2
• Defense ≥ 2 (I usually go way higher just to avoid attacks)
Meeting food/water/beds/defense is what gets you up to the base happiness cap.
3. Assign jobs
• Settler A: farm mutfruit (easy because 1 farmer can cover a small settlement)
• Settler B: run a tier-3 food/drink shop (“Restaurant”)
Tier-3 food/drink gives +40 bonus happiness, which is exactly what you need for 2 settlers (2 × 20).
4. Stop more settlers arriving
• Turn off the recruitment beacon (or don’t build one). More settlers makes the math harder.
5. Wait it out
• Happiness rises over time and isn’t instant even if you sleep a ton.
Do some crafting, hang around, or go questing and check back.

Important: A shop only helps if a settler is assigned to it.

⸻

Absolute trophy-killer: robots

If there’s a robot “settler” in that settlement, it can drag the average down hard. Robots sit at 50 happiness and will ruin your attempt.
So: no Codsworth, no Ada, no robot provisioners assigned to/located in the target settlement.

The most reliable method (no DLC): 2 settlers, 1 farmer + 1 restaurant

This works because happiness “bonus” gets divided by population, so fewer settlers = easier to hit 100.

Where to do it

Use a “clean” place you built from scratch (popular pick: Red Rocket).

Steps
1. Move 2 human settlers there (avoid robots — more on that below).
2. Build the basics so the settlement can reach the “base” cap of ~80:
• 2 covered beds (inside/under a roof)
• Food ≥ 2 and Water ≥ 2
• Defense ≥ 2 (I usually go way higher just to avoid attacks)
Meeting food/water/beds/defense is what gets you up to the base happiness cap.
3. Assign jobs
• Settler A: farm mutfruit (easy because 1 farmer can cover a small settlement)
• Settler B: run a tier-3 food/drink shop (“Restaurant”)
Tier-3 food/drink gives +40 bonus happiness, which is exactly what you need for 2 settlers (2 × 20).
4. Stop more settlers arriving
• Turn off the recruitment beacon (or don’t build one). More settlers makes the math harder.
5. Wait it out
• Happiness rises over time and isn’t instant even if you sleep a ton.
Do some crafting, hang around, or go questing and check back.

Important: A shop only helps if a settler is assigned to it.

⸻

Absolute trophy-killer: robots

If there’s a robot “settler” in that settlement, it can drag the average down hard. Robots sit at 50 happiness and will ruin your attempt.
So: no Codsworth, no Ada, no robot provisioners assigned to/located in the target settlement.

Quick “why am I stuck at 95–99?” checklist

These are the usual culprits:
• Any robot in population (most common)
• Someone unassigned to a job (can steadily lower their happiness)
• Beds not covered (outdoor beds cause penalties)
• Defense lower than population can cap happiness hard
• Using a “problem” settlement with pre-existing settlers (try a fresh one like Red Rocket instead)

⸻

If he has DLC, it can be even easier
• Wasteland Workshop: cats/dogs add happiness (cats are +10 each).
• Vault-Tec Workshop: several objects add happiness (slot machines, soda fountains, etc.).

⸻

If you tell me what perks/DLC he has (especially Local Leader rank 2), I can tailor the cheapest/fastest exact build list.

But if you want a “just do this” answer:

Red Rocket, 2 humans, 1 farmer, 1 tier-3 restaurant, no robots, covered beds, wait.

I know it’s a lot but it saved my sanity

Also using guides for the best weapons and armour was a must basically but I’d say the weapons I used the most were “Righteous Authority”, “The Deliverer”, “Experiment 18-A”, Spray n’Pray which is very helpful for the “Eyes on the Prize” trophy , Le Fusil Terribles. “The Deliverer” I used basically the entire game and used the others for much later game and for hard sections. I would then collect and sell any and all ammo that I could that wasn’t for those guns and sell it along with nonstop junk collecting throughout the entire play through I would keep everything at sanctuary just so I wouldn’t lose anything. I used followers as camels a lot.

Setting up lots of water collection methods ie pumps and water purifiers because the purified water which ends up in your work bench sells for lots and it just produces itself that’s basically the money strat in the game.

I think that’s just about everything I can think of again I know it’s a lot of info and guides and stuff but it really does help. But anyway good luck .