Fallout New Vegas
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Addresses all the bugs related to Caleb McCaffery and his hat. Source: http://fallout.wikia.com/wiki/Caleb_McCaffery. The Atomic Wrangler's room become player's property after finishing the quest.

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Mod version: 1.2
  • If you request Caleb's hat and then kill him without equipping the hat
    it will become permanently embedded in your inventory unable to remove as it is a quest item and cannot be given to the Garrets because they are quite happy he's dead. This presents no issues as quest items carry no weight.[verified]
  • If you kill him in the Atomic Wrangler, his body can be found in the Strip.[verified]
  • His body might remain in the Strip indefinitely when killed.[verified]

Source: http://fallout.wikia.com/wiki/Caleb_McCaffery
Addresses all aforementioned bugs.
Upon death OR the Speech Challenge (40), his hat will no longer be a quest item.
He will disappear from the game once you have finished the quest OR if you killed him either in Atomic Wrangler or in the Strip Area.
New in version 1.2
1. Cleaned-up bugged condition introduced by YUP in VFreeformFreesideSCRIPT, by which Atomic Wrangler's room is set to player's property every 5s (after the quest Debt Collector is finished), for another 150h of gameplay.
2. From the technical point of view, the Atomic Wrangler's room will become player's property after finishing the quest in VFSDebtCollectorSCRIPT. Debt Collector quest will also be properly stopped after finishing it.


The content of my hat.
Jupiter's Great Spot.

Many thanks to:
Nexus - for allowing us sharing our distorted ideas about hats.