Home Sweet Home

Home Sweet Home is a main quest and achievement/trophy $$.

Quick walkthrough

 * 1) Speak to Gage after The Grand Tour
 * 2) Speak to Shank at Nuka-Town USA
 * 3) Select a method for taking over a settlement (Capture, Clear Out, Shake Down, Subdue)
 * 4) Select a gang to use (If Capture or Clear Out was selected)
 * 5) Select a location
 * 6) (Optional) Meet with Lizzie, Dixie and Mason to obtain useful grenades
 * 7) Plant a gang flag at the settlement
 * 8) Return to Shank
 * 9) Meet with Sinner and either talk him down or attack
 * 10) Return to Shank
 * 11) Build objects for the raiders
 * 12) Return to Shank
 * 13) Take over two more settlements
 * 14) Return to Shank

Detailed walkthrough
This quest is obtained upon speaking to Gage after raising the final flag over the fifth of five parks at Nuka-World, cleared out during the course of The Grand Tour. He suggests that with Nuka-World firmly under raider control, it is time to expand to the Commonwealth, establishing raider camps at settlements. He instructs the player character to speak to Shank in order to begin laying the groundwork for the undertaking.

At the entrance to Nuka-Town USA, Shank lays out the steps involved in taking over a settlement, which first requires driving off the existing occupants with either force or persuasion. The player character selects a method, which gang to use in the assault if violence is chosen (Pack, Operators, or Disciples), and finally a location. Shank reviews his notes on the location, to determine if it is possible to attack the settlement, if some other business (such as a quest) needs to be resolved first, or if the occupants are merely beasts (which requires violence as wasteland creatures cannot be negotiated with).

Optional: The player character can meet with Lizzie, Dixie and Mason to obtain grenades that increase persuasion effectiveness, rile up existing settlers to attack each other and draw wild animals to attack the settlement; along with the Smooth Operator chem and recipes for all the aforementioned. While not prompted to, the Sole Survivor can immediately speak to all three raiders after choosing a settlement with Shank to receive all four rewards and recipes. Note that they will often become unavailable after taking the first settlement.

The player character proceeds to the location and secures it for the raiders of Nuka-World, using the workshop to build and plant a flag for the faction it will be handed to. (If violence was employed, the only flag that can be planted is the flag of the gang that aided in the assault.) The player character returns to Shank in Nuka-World, who states the next order of business is to provide resources to the newly-minted raider outpost by strong-arming a settlement near the outpost. Shank makes a few suggestions based on proximity to the outpost and sends the player on their way.

At the chosen settlement, the player character must meet with the leader and convince them, with either payment in caps or intimidation, to supply the nearby raider outpost. The effectiveness of persuasion can be increased and/or the caps payoff amount reduced by having other raider outposts nearby, use of the gangs' optional tools, or building a Nuka-World radio transmitter at the outpost.

Upon returning to Nuka-World once more, Shank informs the player character that a raider named Sinner has caught wind of their activities and is planning to attack. The player character must return to the Commonwealth a third time and head him off. They can either drive him off with a hard Charisma check or with violence. The latter option may prove difficult as some of his allies will be wearing raider power armor. After dealing with Sinner, the player character returns to Nuka-World.

Shank mentions that keeping the gang members happy and loyal is the next step, providing suggestions for objects to build to do just that. At this point, it becomes possible to send Shank to the outpost as a resident, saving the player character the hassle of having to keep returning to Nuka-World to carry out outpost operations.

After building enough objects to keep the occupying raiders entertained, the player character must return to Shank to learn the final piece of the puzzle, which is securing two additional outposts to improve the raiders' presence in the Commonwealth. The happiness does not need to be raised for any of these later settlements; only control of the settlement and raising the gang's flag is necessary. Completing the third raider outpost unlocks the second rank of the Wasteland Warlord perk and additional buildable items. After the third outpost is established, the quest is complete and Power Play begins.

Bugs

 * Depending on how one completes Shake Down, Shank may be stuck in a loop where he continuously says "Don't underestimate the power of beating the stuffing out of someone before you shake them down" followed by "A meal's always tastier when you ain't the one that had to grow it." This prevents him from talking to the player about Sinner so one cannot progress with this quest.
 * This may be fixed by the console command.
 * After completing Home Sweet Home you may not be able to talk to Shank anymore.
 * After accepting from Shank the objective to improve the happiness of the player's settlement, fast-travelling may cause the gangs of Nuka World to inexplicably turn on the player, failing this quest and starting Open Season instead.