Someone to Watch Over Me

Someone to Watch Over Me is a side quest in Fallout: New Vegas.

Synopsis
North Vegas square is a small survivalist community that could use some help enforcing law and order on its streets (and in the sewers). Crandon would pay a mercenary handsomely for their help with the issues.

Walkthrough

 * To start the quest, the player has to talk to Crandon at North Vegas square. The local mayor will give them the lay of the land and explain the situation. The player can use Speech 45 to convince him of his respect for their independence or Barter 35 to show his mercenary side, which will convince Crandon to accept their help.
 * The first task concerns clearing out Squatter Bill and his friends from the playground.
 * The most direct option is to just kill the squatters. This results in New California Republic infamy.
 * A more peaceful solution involves paying the squatters to move off the streets with a Barter check of 45 and 50 caps.
 * Finally, the player can ask nicely. Once. Speech 45 convinces them to move away from North Vegas.
 * If removed peacefully, the squatters return to Westside.
 * Crandon is satisfied with either outcome. The next task includes clearing out a group of Greasers from the sewers beneath the square, who are causing trouble for the residents.
 * The greasers are located in the northeastern section of the sewers, gathered around a burning barrel. Greasy Johnny will rebuff the player, who can:
 * Kill everyone in their way.
 * Pay Johnny off with 100 caps (halving that to 50 caps with Barter 50).
 * Intimidate Johnny with Speech 65.
 * Crandon will be even more jubilant and will offer one final assignment: Helping Mrs. Hostetler in protecting her from the local criminal element, in the form of Andy Scabb. However, before the player can deal with him, they need to talk to Mrs. Hostetler at her household.
 * Mrs. Hostetler will ...
 * Afterwards, the player has to talk to  Jules in the North Vegas square to find that Alice Hostetler is hanging around Andy Scabb and his crew in The Gray.
 * Go to The Gray and get into Scabb's room, either by picking the door (requires Lockpick of 50) or by pickpocketing the room key off one of the thugs guarding the door.
 * Take the henchman message to Andy Scabb underneath the TV and return to Mrs. Hostetler with the evidence.
 * Talk Alice down from killing her mother with a Speech check of 70 or Intelligence check of 7, or through standard dialogue options. Convince her to either stay with her family, or leave and never come back.

Behind the scenes

 * The title of the quest is a cultural reference to the song "Someone to Watch Over Me" written by George and Ira Gershwin for the 1926 Broadway musical Oh, Kay! Considered part of The Great American Songbook, the song has been recorded many times by many artists, including Frank Sinatra, Barbra Streisand, Stéphane Grappelli, Keely Smith, Rosemary Clooney, and Ella Fitzgerald.
 * Greasers were an American 1950s form of youth gang.

Bugs

 * Succeeding in the Speech challenge with Alice and leaving the house without talking to Mrs. Hostetler will fail the quest, as the successful completion hinges on talking to the mother before leaving.