Debt Collector

 is a side quest in Fallout: New Vegas.

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 will get him to pay up. He will give you more caps with a Speech 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 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. The caravan will be down the path to the right. Good loot can be found if you venture further into the cave.
 * If you have entered this cave before receiving this quest the Brahmin will not be in the cave.

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 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 glitch may render the game essentially unbeatable if you kill Caleb. See the Bugs section.

Bringing the hat back to Francine will finish the quest.

Video Walkthrough
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Bugs

 * 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 glitch above.
 * It is possible to accidentally begin this quest by talking to Santiago for the Wang Dang Atomic Tango quest.
 * Following the Santiago bug, you may have already 'collected the debts' when you next talk to Francine Garret. After being told that McCaffery has fled the casino and exiting the chat, McCaffery will still be in the casino and will turn hostile. McCaffery will then be killed by the casino guards thus completing the quest without negative karma.
 * After this bug Francine and other key characters in the Wrangler may be killed. To avoid this, leave the Wrangler as soon as the fire fight starts, on returning only McCaffery will have been killed.
 * When asked to kill McCaffery, there's a possible glitch where you will be unable to select any dialogue options.
 * 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.
 * It appears the crash only affects entering via the North gate. On the PC the crash doesn't occur until you pass the Old Mormon Fort. It is possible to enter Freeside via the East Gate without crashing.
 * Upon completing this quest and sleeping in the bed found in the Atomic Wrangler, any attempts to leave the room will result in a black screen crash.
 * The Brahmin corpse in Broc Flower Cave is missing if you have entered the cave before starting the quest. The quest marker will only point to a patch of blood on the ground, making it impossible to get the caps from Lady Jane's caravan. Thankfully, you can lie about collecting the caps and pay off all the debts yourself. You can also place Jane's Brahmin near you using the console (PC). Enter.
 * Upon completing the quest, Francine Garret will disappear if you leave and re-enter the casino.
 * It is possible that Grecks may not be able to be located.
 * 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.
 * McCaffrey's dismembered head being rendered with semi-transparent hat on after hat taken from his corpse.
 * 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.
 * If you kill Santiago the quest will not update and Francine's dialogue will not reflect Santiago's death. If you kill him after already collecting from him, it will say that you still need to collect from him.
 * . 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.
 * If choosing to obtain Caleb McCaffrey's hat peacefully through a speech check, putting on his hat afterwards causes the game to freeze.

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