The crazed raider went inside the Crash House, at an unknown time, and held the hooker Sinthia hostage. It isn't clear if the Vault Dweller ever encountered this raider, considering his memoirs make no mention of him killing or helping the raider with his "money" problems.
The crazed raider will ask for a mere 100 bottle caps, and to be able to walk away unscathed from the kidnapping. This option will give the most experience for the quest, and results in Sinthia becoming more 'friendly' with the Vault Dweller. However, to even get the raider to co-operate, a few Speech checks must be passed, and one may not insult or try to intimidate the raider.
Almost all of the normal dialogue options with the man result in him attacking, or if failing a Speech check. Any insult triggers this, but some options lead to him killing Sinthia first, making it impossible to finish the quest. In combat, he is about as strong as a normal Khan raider, wielding a 10mm pistol. A few results of killing him in combat are Sinthia's distaste in the player character's methods, and the considerably smaller amount of experience earned for the quest. She will not speak to the Dweller in case of this outcome.
It is also possible to knock out the raider with a sneak attack with him subsequently carried out of the room. this will result in Sinthia being skeptical of the player but eventually calming down and offering her "services" later. This option offers less experience than persuading the raider to calm down and cooperate.