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I'm at a shop and these caps are burning a hole in my Vault 111 Jumpsuit, but I know there's some way to maximize my cash. What are my options? Raising my Charisma through the roof and buying the Cap Collector perk? Anything else? And how much do those things actually drive prices down?

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Obviously there are ways to increase your income, but I'm considering that outside the scope of this answer, and focusing on getting better prices.

Discounts

Some vendors will give you discounts for actions taken in the game, like Carla giving you a discount for making a sarcastic remark when you meet her. Shopping at vendors that give you a discount will help.

Raising Charisma

Much like raising intelligence for additional xp, you can raise your charisma for better prices. I keep a set of charisma gear on me, including clothes (+1-3 CHA), a hat (+1 CHA), and glasses (+1 CHA). I put these on before speaking with vendors, and it improves both buying and selling prices.

As an experiment, my character with 3 CHA sold some items without the CHA equipment (3 CHA), then I loaded and sold the same items with the equipment (7 CHA). I got approximately 200 caps without, and approximately 250 caps with.

You could also drink some alcohol first, which should pay for itself.

Perks

There's a perk for better buying and selling prices, called Cap Collector. I haven't tried this, but the exact numbers are listed on the fallout wikia.

You can also improve buying and selling prices with the perks you receive from finding Tales of Junktown Jerky Vendor magazines.

Other Items

Some specific items will give you a boost specifically to prices. Grape Mentats will give you 10% better prices and +5 Charisma for 8 minutes.

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  • Also grape mentats give you 10% better prices for 5 mins
    – Yasskier
    Nov 19, 2015 at 0:20
  • @Yasskier Added, thanks. The wiki says 8 minutes.
    – DCShannon
    Nov 19, 2015 at 1:15

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