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Debt Collector - Introduction
This is a very easy job to get. You just need to talk to Francine Garrett and ask for work. She'll mention that there are a few people with outstanding tabs and that it adds up to 600 caps. You can get 150 for collecting them, or with some skill in Barter you can get 300.
Note that this debt collection can be really easy. All the people are around Freeside and they can generally be talked into paying without much trouble.
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Debt Collector - Grecks
Grecks is the first one you should probably collect from, since he's the easiest. He's actually begging for money and staying at a squatter camp. If you approach him then he should actually volunteer to pay it back. You should be able to do it with just the normal options.
Note that if you have more than 40 points in Speech, you can convince him that he owes more and take the rest of his money for yourself. With 60 Speech, you can even get him to give up his clothes.
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Debt Collector - Santiago
Santiago is another fairly easy collection. You have a few good options that don't require any special skills. Note that his special code for Mick and Ralph's is a scam, although you do get some experience from getting him to cut the price for it in half through Barter.
The first is to follow Francine's advice. Santiago is just putting on his whole "VIP" act. If you hit him through the dialogue option (don't actually attack him), then he'll fold and pay up. As with Grecks, you can use SPeech to convince him to pay more than he has to.
If you have more than 50 points in Speech you can convince him that Francine was angry enough to put a bounty on his head. He'll also fold and pay up.
The last option is a bit interesting. If you're doing "Wang Dang Atomic Tango" for Francine's brother, you can offer to hire Santiago as the Smooth-Talker/Real Boyfriend. He should happily agree to it and pay off his debt through his work.
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Debt Collector - Lady Jane
Now, she's not lying. She really did lose a caravan. It's inside Broc Flower Cave and it has the necessary caps onboard. If you want to dungeon crawl, kill some giant rats and find a unique version of the Varmint Rifle, the Ratslayer, then feel free to go and check. Note that the caravan should be there regardless. If it isn't, then it's an unrelated bug. Lady Jane does have the money. She's just using the caravan as an excuse and hopes to get you to recover it for free.
If you can beat one of the various skills checks, you should.
If you have Perception higher than 7, you can "see" through her lie and get her to admit to having a backup fund to pay off the full debt.
If you have more than 40 points in Barter or Speech, you can ask if she has something of value. She'll pay about half of the debt and pay for the rest with some sensor modules and cartons of cigarettes. If you're looking for sensor modules to fix ED-E, then this isn't a bad option.
Lady Killer should give a similar option too.
Regardless of how you get the caps, turn them in to complete the mission.
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Debt Collector - Caleb McCaffery
Once you turn in the 600 caps owed to Francine Garrett, she'll give you a new mission. Their old mercenary, Caleb McCaffery, isn't happy that she gave you what should have been his work. So he robbed the place and took off for the Vegas Strip.
The toughest part of this may just be getting into Vegas. You can either help the King, befriend the NCR or raise 2,000 caps to pass the credit check at the gate.
Once you're inside, it's really easy. Caleb should just stand around outside the Lucky 38 casino. Just confront him and make your decision. If you have more than 40 points in Speech, you can convince him to just pay you off and hand over his hat to fake his death. Or you can tell him that you're going to kill him. This should make him hostile. In my fight, it didn't seem to anger the Securitrons. If you have trouble with this, you may want to just hang back and let your companions kill him. He uses a caravan shotgun, so try to stay back a bit. Otherwise, it's a fairly easy kill for someone with half decent equipment.
Take the hat off of his body and give it to Francine to complete the mission and get your reward.
Freeside in Fallout: New Vegas has a number of interesting side quests to do. You'll need to handle the King's struggle, help the Followers of Apocalypse stabilize the area, recruit some new escorts for the Atomic Wrangler and collect some overdue bar tabs for the Garretts.