i enjoy the updates. it's fun hearing someone else's playthrough. Everyone has different experiences. sorry you wound up short on caps. if you ignore the point of dead money to spite chris avellone you will have enough caps guaranteed tho.
To break the economy, I just take the Jury Rigging perk, max out Sneak, and start genociding NCR troopers with my silenced sniper rifle. Once you get enough NCR dogtags, you can hand them over to the centurion at Cottonwood Cove for Legion fame, which will eventually result in a frumentarius hunting you down and giving you the Caesar's Favor quest, which is the Legion equivalent of the NCR Emergency Radio (but this one actually works). Every 3 days or so, you can go back to the boxes on the hill above Cottonwood Cove to pick up the confiscated contraband they've left for you, and if you've reached idolized status, you're guaranteed to find either recon armor or metal armor. Thanks to Jury Rigging, I can use the metal armor to patch up my power armor, and use the NCR armor I've been hoarding to fully repair the recon armor to full condition (base value: 7,200 caps) and sell it for obscene profit, and I can do it twice a week. Best of all, if you're idolized by the Legion, unless you kill Caesar your reputation can't ever go low enough to get the boxes taken away or have hit squads sent after you. I know some people like to fight the hit squads and loot their high-level gear, but I find the boxes to be a better option.
I also routinely buy all the corn from Farber at Camp McCarran every time I go back there to buy more drugs from Contreras and then have the pervert machine at the Sink convert it to Salient Green to increase its value tenfold. And I also take the Them's Good Eatin' perk to be able to loot Blood Sausage or Thin Red Paste off my numerous victims since they both sell for insane prices. (edit: Don't forget to hoard empty bottles of all types, since the faucet at the Sink can convert them into Purified Water and increase their value up to twentyfold.)
As for spiting Chris Avellone, Cass serves as his mouthpiece during the end slides if she lives, so I always recruit her, do her quest if I want the XP, and then slip a stick of dynamite into her pocket back at the Lucky 38. (Arcade Gannon is Josh Sawyer's mouthpiece, is gay, and talks like a Redditor, so I do the same to him unless I'm doing a Legion run and can sell him into slavery, although one day I might do the thing where you complete his companion quest, convince the Remnant to fight for the NCR, and then side with the Legion to get the end where his armor is recognized by NCR rangers during the retreat and he spends the rest of his life imprisoned as an Enclave war criminal.)