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Someone to Watch Over Me - Squatters
You can find the entrance to North Vegas Square just to the west of the north entrance to Freeside. If you go inside the small community, you'll find two mercenaries patrolling the street. Talk to Crandon and use either 35 points in Barter or 45 points in Speech to convince him that you'll be a useful ally for the area. He'll pick you up for a little quick mercenary work.
The first mission is a quick one. You just have to take care of the squatters that set up on the playground. You have the option of attacking and killing them, but note that they are NCR citizens. Killing them will probably hurt your reputation with the NCR. You have options to either bribe them with a 45 point Barter check or use your 45 points in Speech to make them leave.
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Someone to Watch Over Me - The Greasers
Once you take care of the squatters, Crandon will ask you to go into the sewers below the area and find some greasers that are harassing people in the town.
The sewers are a bit of a nightmare. You'll need to rely on your local map and the marker to find Johnny, their leader. Once you track him down, you'll have a few options.
You can just kill them. Just take him down fast. He's not wearing much armor, so I doubt it will be much of a challenge.
With 65 points in Speech, you can convince him that he'll be facing an angry mob soon. He'll leave peacefully.
You can just pay him 100 caps and call it a day. 50 points in Barter reduces this to only 50 caps.
Regardless of how you take care of the greasers, backtrack to the ladder and report back in to Crandon.
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Someone to Watch Over Me - Helping Mrs. Hostetler
This fairly unfriendly woman has been having family trouble lately. Crandon wants you to help her out, so just walk over to her house. It's a short distance from North Vegas Square. Go inside and talk to her and explain that you're with Crandon to get her to open up about her issue.
Go back to North Vegas Square and talk to Jules. He can direct you to Alice and her new friend, Andy Scabb. Andy lives inside The Grey, the damaged apartment building at the end of the street. Go inside and turn to the left to quickly find Andy's room. There's a guard standing outside it, so it's easy to see.
With 70 points in Speech, you can convince him that Mrs. Hostetler is outside with a shotgun. That makes him abandon his post. Otherwise, you'll just need to wait and hope he walks away, or kill him. No one seems to care if you kill him.
Pick the lock or use the guard's key to get into Andy's room. The only thing of interest is a note lying underneath his TV. Read the note to learn about Andy's cold-hearted plot and secure the evidence that you need. Unfortunately, on your way out, you'll run into Andy.
He'll either want to know about the dead guard, or he'll wonder why you sent his guard outside. 65 points in Speech will keep him peaceful with a simple lie. If not, you may have to take him out too. Again, it shouldn't really matter. It's up to you and he's not too tough on his own.
Run back to The Hostetler house to find Alice in the middle of a robbery. They're in a bit of a standoff, so it's up to you to decide the outcome. There are a bunch of different ways that this can end. The basic divide is whether you want to rob Mrs. Hostetler or not.
With 7 points in Intelligence or 70 points in Speech, you can immediately talk Alice down. It should also be possible to do it without any skills, if you call Alice's bluff with actually goading her into attacking. You can then get her to hand over the gun and calm down. I believe you can also convince her to go ahead and do it. This nets you some negative karma and saves you the trouble of killing Mrs. Hostetler yourself.
If you talk Alice down, you can either convince her to stay or support her decision to leave. Again, it's basically just for story purposes, although Mrs. Hostetler won't be that happy if you let Alice leave.
Once the situation is settled, talk to Mrs. Hostetler.
If you want to rob her, choose the attack option. She's very good with her shotgun, but she's not wearing any armor. She'll die quickly as long as you can survive the first blast. You can get 1000 caps off of her body.
If you are happy with helping her, either ask for a reward or just settle for good karma.
This will also officially complete the quest. Crandon doesn't have anything else for you.
New Vegas is a fairly dense quest hub, with a number of side quests to do for various side factions. I'll cover how to help Emily Ortal spy on Mr. House, how to help a sign maker find his inspiration, how to help a wayward girl in North Vegas and how to break up a gang of cannibals in New Vegas.