Debt Collector

Debt Collector is a side quest in Fallout: New Vegas.

Detailed walkthrough
Talk to Francine Garrett at the Atomic Wrangler, and ask if she needs any work done. She will inform you there are three individuals in Freeside that owe the casino caps. In total it will be 600 caps owed, and you will gain 150 caps if you return the caps to Francine (300 with a Speech check of 50). The three individuals are Grecks, Santiago, and Lady Jane. You can pay out of your own pocket if you wish.
 * Grecks is located behind the Old Mormon Fort. He will give you the money with either a Speech check or a punch to the face (through dialogue). A second Speech check of 40 or higher will net you additional caps, and a third of 60 will cause him to give you the clothes off his back (negative Karma).
 * Santiago is located behind the collapsed building opposite Mick & Ralph's. He will try to talk his way out of it, but revealing that there's a bounty on his head or punch him in the face will get him to pay up. He will give you more caps with a Speech check. If you have the Wang Dang Atomic Tango quest also active at the same time, you can convince him to work off his debt at the Atomic Wrangler, also completing the suave talker portion of that quest. Doing this, you'll only have to return to Francine with the 388 caps from the other 2, but will still get your full reward for collecting the debts (150 or 300 caps, depending on the earlier barter check).
 * Lady Jane is located to the right of The Strip North Gate. You can either get the money through a Speech Check of 40, a Barter check of 40, or the Lady Killer perk. With a Perception of 7 or higher, your character will be able to tell she is lying and get the caps. You could also ask for other things to help pay off the debt. Doing this results in her giving you 156 caps and 94 caps worth of sensor modules and cartons of cigarettes (neither killing or pickpocketing her at this stage of the quest will work. Doing either would result in you having to collect caps from her caravan). Failing that, she'll direct you to the caravan she lost in the Broc Flower Cave, good loot can be found if you venture further into the cave. You can also fail all checks and another option will show up for threatening her. She will ask you to tell the Garrets she's dead, to which you reply you don't like liars. Choosing this option will turn her hostile, allowing you to kill her and collect the 256 caps (she will have a bag of bottle caps on her corpse).
 * If you have entered this cave before receiving this quest the brahmin will not be in the cave.
 * The brahmin will not spawn until you agree to retrieve the debt this way.

Once those three are done, Francine will give you a fourth assignment. Her former collector, Caleb McCaffery, skipped town with a large sum of caps, and she wants him dead. His hat needs to be taken as proof.
 * Caleb is in The Strip, in the first section near the gate to the second. With a Speech check of 40, he'll give you his hat and the stolen caps. Otherwise, you'll need to kill him for it. Note that the entrance to the Strip will require that you have at least 2000 caps (not as payment, but merely checked against as a minimum necessary value), a passport, or pass a Science check of 80. Alternatively, you can simply use the Monorail if you are good with the NCR and have not let it be destroyed in I Put a Spell on You.
 * On consoles, a major bug may render the game essentially unbeatable if you kill Caleb. See the Bugs section.

Bringing the hat back to Francine will finish the quest.

Bugs

 * If you finished the first part of the quest and returned with the caps to Francine Garret, you may be able to get double the caps. When you get to Santiago, ask about the free vip and his discount with Ralph's brother. Later on you will find out it was a fake but will unable to bring up again to Santiago if you collected the caps. Before killing the twins old bounty hunter, do James Garret quest on more hookers. Once you go back to Santiago you have the option to tell him about his fake discount. Once you finish that part you can now chase after their old bounty hunter. Get his hat and return to Francine Garret. She will bring about the old quest you already finished and give you the reward again.
 * If you have already completed the quest Wang Dang Atomic Tango and hired Santiago as the suave talker, there is a possible bug that you will not be able to talk to Santiago to collect the chips. Its still possible to complete the quest by pickpocketing the bag of bottle caps off of him.
 * Upon completing this quest and killing McCaffery, any attempts on re-entering the Strip will result in a black screen crash and the autosave corrupting (some users have reported The Strip door also requiring a key). To fix the black screen crash, wear the Old cowboy hat (or even Caleb McCaffery's hat) that you can find at Crimson Caravan's store (it's near a bunch of first aid boxes). Wearing it before entering The Strip from Freeside will stop the game from crashing. The key-requirement for The Strip gate can easily be solved by taking the NCR monorail in Camp McCarran to the Strip, and then opening the gate from the inside. If you cannot use the monorail, stealthily kill one of the Securitron guards near the gate and loot the key from its corpse.
 * To avoid the black screen crash, try not to decapitate Caleb; if McCaffery's body is intact when you remove the hat and other items from it, the visual of the hat disappears from the corpse. It is unclear why this was occurring but when his head separated from the rest of the corpse, the image of the hat on McCaffery's head remained even when his corpse was looted, causing the bug above.
 * When asked to kill McCaffery, there's a possible bug where you will be unable to select any dialogue options. (Pressing start when this happens will fix it)
 * Following closure of the dialog when asked to kill McCaffery, he may be involved in a firefight inside the Atomic Wrangler. He will appear friendly in V.A.T.S. and be fighting with Wrangler staff. You can kill him here and get the reward before entering the Strip.
 * If Caleb McCaffrey is the first bounty you get and complete by passing a speech check, returning to Francine Garret will complete the mission without having to find Grecks and Lady Jane.
 * If you go after Caleb McCaffery before Lady Jane, you complete the quest. However, his room doesn't not become yours, despite Francine awarding it to you, all items in it are still 'owned' by someone else and you cannot sleep in the bed.
 * In some cases, there is a bug that if you kill Caleb McCaffrey before you start this quest, you will not be able to complete it or if you pick up McCaffrey's hat, you won't be able to drop it, as it will still be marked as a quest item.
 * . The player may be unable to ever open dialogue with Lady Jane. (Attempting to simply triggered a passive statement about ED-E) Repeated attempts caused her to repeat the statement. This can be very problematic and render the quest unable to be completed without killing or pickpocketing her. No known fix as of yet, reloading a save or re-entering the cell does not work.
 * . It's possible to turn in the quest with Francine before it's finished and thereby adding Caleb McCaffrey to the existing questline but at the same time making it impossible to talk to Lady Jane.
 * . You should not do this quest and Wang Dang Atomic Tango at the same time. Otherwise, you can only return 388 caps to Franchine, it's 250 from Jane and 138 from Grecks. The game will assume that you didn't collect money from Santiago.
 * . Even if you finished the quest, the items in the room still owned by another person. You can only sleep in the bed for free.
 * Santiago sometimes will disappear and is nowhere to be found, or he will be found dead and his bottle caps won't be on his body.
 * . If you get the caps from Lady Jane with Lady Killer perk after you talked about her caravan, finding Jane's caravan will be still an optional quest. However sometimes the brahmin sometimes will not spawn thus leaving you without the extra caps. The side-quest can be still completed without the optional side-quest.
 * If you kill Santiago after receiving his debt, the journal entry 'Collect 212 caps from Santiago' will uncheck, and a quest marker will appear on his body. You can, however, still complete the quest normally by turning in 600 caps to Francine and dealing with McCaffrey afterwards.
 * Sometimes Jane's brahmin does not spawn. To fix this with the console type player.placeatme 00116af4 1, this will spawn the brahmin alive, kill it loot it and you're done. I only tried spawning the brahmin in the cave about where it should be but I think it will work anywhere.

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