Debt Collector

 is a quest in Fallout: New Vegas.

Quick 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 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. The three individuals are Grecks, Santiago, and Lady Jane. Note than you can also give Francine 600 of your own caps and tell her that you collected all of the debts. This is how:

-Obtain caps from Grecks. Talk to him in Freeside (behind the Mormon Fort) and he will give you the money with either a speech check or a punch to the face (through dialogue). You can also get him to give you more caps with a speech of 40 or higher. He will give you his clothes with a speech of 60 or higher.

-Obtain caps from Santiago. Just ask him, and he will give it to you after you listen to his act and threaten him. He will give you more caps with a speech check.

-Obtain caps from Lady Jane through a Speech Check, or Lady Killer perk, or obtaining the caps from her caravan in Broc Flower Cave. 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.)
 * In 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, though.

-Kill Caleb McCaffery, and loot his hat, or you can go choose a speech check (of 40) and convince Caleb to give you his caps and hat.
 * You will need access to The Strip, which will require you have at least 2000 caps (which do not get removed) or a passport.

-Bring Caleb's hat back to Francine Garret for your reward.

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 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. The three individuals are Grecks, Santiago, and Lady Jane.

Grecks: Fairly straight-forward, if you tell him you are with the casino and will be harmed if the caps are not returned, he will hand over the caps. Greck located behind Fort Mormon.

Santiago: Santiago will deny that he owes caps, but a punch to the face (in dialogue), and he will quickly hand over the caps. Also a Speech Check (50) threatening him will work as well. If you have already spoken to James Garrett and agreed to the Wang Dang Atomic Tango quest, you can convince Santiago to become an escort, which will result in his debt being paid. Santiago located behind ruined building across from Mick & Ralphs in Freeside. He also says that you can get a discount at Mick and Ralph's but this is reported to be a hoax.

Lady Jane: The hardest to obtain caps from. She does not deny that she owes caps, but her caravan was lost in Broc Flower Cave. She will hand over the caps immediately with a Perception check (7), a barter check (40), or a speech check (40). Alternatively, you can travel to the rat infested cave and retrieve the caps from the caravan, but if you have the Lady Killer perk you will have a unique dialogue option and she will hand over the caps immediately. Note that the caps from the caravan in Broc Flower Cave will still be there for the player's taking after you get the caps directly from Lady Jane. Lady Jane located by The Strip North Gate in Freeside.


 * Enter the Broc Flower Cave and take the path that leads to the right, follow it down and when you enter a big room filled with Giant Rats the dead Brahmin will be to your left. Further down the cave to the right will be a path that leads you to the room which contains the Ratslayer a unique Varmint Rifle. If you have the Wild Wastelands perk on the cave will insted be filled with a tougher version of giant rat called Rodents of unusual size, a refference to the Princess Bride.

Killing Caleb McCaffery: You will need access to The Strip, which will require 2000 caps, or a passport, or Science 80. When you find Caleb, you will either have to kill him or have a speech of 40 and convince him to give you his hat. He can be a tough opponent, at close range his caravan shotgun can do high damage. When you kill him he will have 20 gauge ammo and slugs on him, as well as his gun, his hat, and duster. When Francine is informed she will award you with another 150 caps, and McCaffery's room. (which can be used as a player house)


 * (Optional) You can convince Caleb McCaffery to give you his hat and a few credits via passing the 40 speech check and after this you are free to kill him and loot his corpse for an additional 150-160 caps. Killing him after negotiating will not incur any penalties with anybody and you will not be attacked for "murdering" him but will cause you to lose karma.

Bugs

 * It is possible to accidentaly begin this quest by talking to Santiago for the Wand 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.


 * To avoid the black screen crash do not use the controller while the screen is black. The game will load after about 30 seconds (on a hard drive installation, probably longer without one).


 * When asked to kill McCaffery there's a possible glitch where you will be unable to select any dialogue options. (At least, this can be the case on the Xbox 360.)


 * 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. (360)

This is probably a pretty rare bug because on all my characters this bug still hasn't been triggered (I always kill him)
 * Upon completing this quest and killing McCaffery, any attempts on re-entering the strip will result in a blackscreen crash and the autosave corrupting (some users have reported The Strip door also requiring a key). To fix the blackscreen crash, Wear the old cowboy hat that you can find at Crimson Caravan's store. (it's near a bunch of medkits). Wearing it before entering the strip from freeside will stop the game from crashing. (Xbox 360) (Not Confirmed - This doesn't always happen. (At least not for me.)) 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.

-(This bug is true, I can confirm it. Following me killing McCaffery, I went and slept with Beatrix (the ghoul), upon finishing and going to leave, I was struck with the black screen crash. I am now stuck in her room. Before killing McCaffery you should save a couple files just in case.) - BlindedByScience


 * Upon completing this quest and sleeping in the my bed found in the Atomic Wrangler, any attempts to leave the room will result in a blackscreen crash.


 * The brahmin corpse in Broc Flower Cave is missing for some players. Thankfully, you can lie about collecting the caps and pay off all the debts yourself.


 * 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 (Xbox 360 - Confirmed)


 * McCaffrey's dismembered head being rendered with semi-transparent hat on after hat taken from his corpse.