The audio quality of a USB to headphone jack can vary wildly as they need to contain their own DAC (digital->analoge converter), tbh most are probably good enough for most people but depending on your headphone setup you may be able to tell. (Depending how much you spend they can actually have better audio quality than a normal phones headphone jack)
Edit: Fiio makes a pretty nice one, but not the cheapest on the block
Forgive me if I didn't detect the sarcasm. But the color is goodwills discount system. On any given day the red tags might be discounted, or the blue. It is a way to clear out stuff more consistently.