Sanctuary
Complete “Sanctuary”
Will unlock as you progress through the main story.
Community Organizer
Ally with Three Settlements
Simply clear out and establish three settlements. This one is easy and Preston will provide you with quite a few locations at the beginning of the game.
Benevolent Leader
Reach Maximum Happiness in a Large Settlement
This one requires a bit of work. To make a settlement large, you have to send all of your companions to the same one. Sanctuary is probably best for this, since it starts with a handful of people already. To increase their happiness, make sure all their needs are met and even throw in some electricity and decorations. Check in often and you’ll have this trophy/achievement in no time.
Gun-For-Hire
Complete 10 Side Quests
Side Quests are any quests that aren’t part of the main quest line. You’ll come across a ton of these, especially if you’re doing the faction quests.
Mercenary
Complete 50 Misc. Objectives
Miscellaneous objectives are provided in a number of ways. Some can be overheard by standing near guards in any city, others are given by NPCs. They are all filed under one quest, so just complete any 50 of them.
Scavver
Gather 1000 Resources Used For Crafting
Just pick up everything and it will pop up eventually.
What’s Yours Is Mine
Pick 50 Locks
It’s just as it reads. Keep in mind that it must be you who picks the locks. Having a companion do it does not count. There are a lot more than 50 locks in the game, so you should acquire this long before you’ve completed any of the quest lines.