So now I'll have to pay $100 for a headphone with the quality of a $7 one while getting zero benefits and tons of incompatibility issues. That's "progress" all right. Progress for Apple's bottom line at the expense of every consumer who buys the new devices and headphones. It's just too bad consumers are too stupid to see how they're being fucked over.
A halfway decent DAC will cost closer to $50 than $1. Given the current market for marked-up mediocre headphones, I can much more easily see the parent's scenario than yours.
It's likely integrated with another chipset, but I don't imagine it's more than $10-20. However, to be standalone, there has to be a dedicated DAC, Amp, and power supply chipset, as well as the associated resistors and capacitors; which when not integrated into another package (like a phone motherboard) is not as cheap.
The least expensive USB set I've found in the past has run around $30, and you get what you pay for. Good enough for highly compressed voice communication, but terrible at rendering music.